Heterocyclic dicarboxylic acid diamide derivatives, agricultural/horticultural insecticides and method of using the same

ABSTRACT

Heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I):                    
     wherein R 1 , R 2  and R 3  represent each H, optionally halogenated C 3-6  cycloalkyl, etc.; Het represents a 5- or 6-membered heterocycle; X and Y represent each halocyano, nitro, optionally halogenated C 3-6 , cycloalkyl, optionally substituted phenyl, an optionally substituted heterocycle, etc; n is from 0 to 3; m is from 1 to 5; Z 1  and Z 2  represent each O or S; and B 1  to B 4  represent each C or N. Agricultural/horticultural insecticides having an excellent controlling effect on pest insects such as diamond-back moth ( Pluntella xylostella ) and tobacco cutworm ( Spodoptera litura ).

This application is the national phase of international applicationPCT/JP00/04136 filed Jun. 23, 2000 which designated the U.S.

TECHNICAL FIELD

The present invention relates to heterocyclic dicarboxylic acid diamidederivatives, agricultural and horticultural insecticides containing anyof said compounds as an active ingredient, and their usage.

BACKGROUND ART

JP-A-6-25190, JP-A-9-323974, WO9944992, JP-A-12-7661, JP-A-12-103708 andthe like disclose compounds constituting a portion of the heterocyclicdicarboxylic acid diamide derivative of the present invention but do notdescribe or suggest the usefulness of the disclosed compounds asagricultural and horticultural insecticides at all.

The present inventors earnestly investigated in order to develop a novelagricultural and horticultural insecticide, and consequently found thatheterocyclic dicarboxylic acid diamide derivatives represented by thegeneral formula (I) of the present invention are novel compounds notknown in any literature and that not only these compounds but also thecompounds disclosed in the prior arts can be put to a novel use, wherebythe present invention has been accomplished.

DISCLOSURE OF THE INVENTION

The present invention relates to heterocyclic dicarboxylic acid diamidederivatives represented by the general formula (I):

{wherein R¹, R² and R³, which may be the same or different, are hydrogenatoms, (C₃-C₆)cycloalkyl groups, halo(C₃-C₆)cycloalkyl groups or—A¹—(R⁴)r (wherein A¹ is a (C₁-C₈)alkylene group, a (C₃-C₆)alkenylenegroup or a (C₃-C₆)alkynylene group, R⁴, which may be the same ordifferent, are hydrogen atoms; halogen atoms; cyano groups; nitrogroups; halo(C₁-C₆)alkyl groups; (C₃-C₆)cycloalkyl groups;halo(C₃-C₆)cycloalkyl groups; (C₁-C₆)alkoxycarbonyl groups;di(C₁-C₆)alkoxyphosphoryl groups whose (C₁-C₆)alkoxy groups may be thesame or different; di(C₁-C₆)alkoxythiophosphoryl groups whose(C₁-C₆)alkoxy groups may be the same or different; diphenylphosphinogroups; diphenylphosphono groups; phenyl groups; substituted phenylgroups having one or more substituents which may be the same ordifferent and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups;heterocyclic groups; substituted heterocyclic groups having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A²—R⁵ (wherein A² is —O—, —S—,—SO—, —SO₂—, —N(R⁶)— (wherein R⁶ is a hydrogen atom; a(C₁-C₆)alkylcarbonyl group; a halo(C₁-C₆)alkylcarbonyl group; a(C₁-C₆)alkoxycarbonyl group; a phenylcarbonyl group; a substitutedphenylcarbonyl group having one or more substituents which may be thesame or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aphenyl(C₁-C₄)alkoxycarbonyl group; a substitutedphenyl(C₁-C₄)alkoxycarbonyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a (C₁-C₆)alkylsulfonyl group; or ahalo(C₁-C₆)alkylsulfonyl group), —C(═O)— or —C(═NOR⁷)— (wherein R⁷ is ahydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a(C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynylgroup; a cyclo(C₃-C₆)alkyl group; a phenyl(C₁-C₄)alkyl group; or asubstituted phenyl(C₁-C₄)alkyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups), and R⁵ is a hydrogen atom; a(C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; ahalo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynylgroup; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a(C₁-C₆)alkoxy(C₁-C₆)alkyl group; a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; aformyl group; a (C₁-C₆)alkylcarbonyl group; a halo(C₁-C₆)alkylcarbonylgroup; a (C₁-C₆)alkoxycarbonyl group; a mono(C₁-C₆)alkylaminocarbonylgroup; a di(C₁-C₆)alkylaminocarbonyl group whose (C₁-C₆)alkyl groups maybe the same or different; a mono(C₁-C₆)alkylaminothio-carbonyl group; adi(C₁-C₆)alkylaminothiocarbonyl group whose (C₁-C₆)alkyl groups may bethe same or different; a di(C₁-C₆)alkoxyphosphoryl group whose(C₁-C₆)alkoxy groups may be the same or different; adi(C₁-C₆)alkoxythiophosphoryl group whose (C₁-C₆)alkoxy groups may bethe same or different; a phenyl group; a substituted phenyl group havingone or more substituents which may be the same or different and areselected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a phenyl(C₁-C₄)alkyl group; asubstituted phenyl(C₁-C₄)alkyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a heterocyclic group; or a substitutedheterocyclic group having one or more substituents which may be the sameor different and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups), and ris an integer of 1 to 4),

provided that R¹ and R² are not hydrogen atoms at the same time,

R¹ and R² may form a 4 to 7 membered ring by combining to each other, inwhich the ring may contain the same or different 1 to 3 hetero atomsselected from the group consisting of oxygen atom, sulfur atom andnitrogen atom,

Het is a heterocyclic group represented by any of the following formulasQ1 to Q22:

 (wherein X, which may be the same or different, are halogen atoms;cyano groups; nitro groups; (C₃-C₆)cycloalkyl groups;halo(C₃-C₆)cycloalkyl groups; tri(C₁-C₆)alkylsilyl groups whose(C₁-C₆)alkyl groups may be the same or different; phenyl groups;substituted phenyl groups having one or more substituents which may bethe same or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups;heterocyclic groups; substituted heterocyclic groups having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A³—R⁸ [wherein A³ is —O—, —S—,—SO—, —SO₂—, —N(R⁶)— (wherein R⁶ is as defined above), —C(═O)—,—C(═NOR⁷)— (wherein R⁷ is as defined above), a (C₁-C₆)alkylene group, ahalo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylene group, ahalo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R⁸ is as follows:

(1) when A³ is —O—, —S—, —SO—, —SO₂— or —N(R⁶)— (wherein R⁶ is asdefined above), then R⁸ is a halo (C₃-C₆)cycloalkyl group; ahalo(C₃-C₆)cycloalkenyl group; a phenyl group; a substituted phenylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; a substituted heterocyclic group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or -A⁴—R⁹ (wherein A⁴ is a(C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₁-C₆)alkenylenegroup, a halo(C₃-C₆)alkenylene group, a (C₁-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R⁹ is a hydrogen atom; a halogen atom;a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a(C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted phenyl grouphaving one or more substituents which may be the same or different andare selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A⁵—R¹⁰ (wherein A⁵ is —O—, —S—,—SO—, —SO₂— or —C(═O), and R¹⁰ is a (C₁-C₆)alkyl group; ahalo(C₃-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenylgroup; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; aphenyl group; a substituted phenyl group having one or more substituentswhich may be the same or different and are selected from halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthiogroups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; or a substituted heterocyclic group having one ormore substituents which may be the same or different and are selectedfrom halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups)),

(2) when A³ is —C(═O)— or —C(═NOR⁷)— (wherein R⁷ is as defined above),then R⁸ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkylgroup; a (C₂-C₆)alkenyl group; a halo(C₂-C₆)alkenyl group; a(C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxygroup; a (C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; adi(C₁-C₆)alkylamino group whose (C₁-C₆)alkyl groups may be the same ordifferent; a phenyl group; a substituted phenyl group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a phenylamino group; a substitutedphenylamino group having on the ring one or more substituents which maybe the same or different and are selected from halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthiogroups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; or a substituted heterocyclic group having one ormore substituents which may be the same or different and are selectedfrom halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups, and

(3) when A³ is a (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a(C₂-C₆)alkenylene group, a halo(C₁-C₆)alkenylene group, a(C₂-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group, then R⁸ is ahydrogen atom; a halogen atom; a (C₃-C₆)cycloalkyl group; ahalo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; atri(C₁-C₆)alkylsilyl group whose (C₁-C₆)alkyl groups may be the same ordifferent; a phenyl group; a substituted phenyl group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a heterocyclic group; a substitutedheterocyclic group having one or more substituents which may be the sameor different and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; or—A⁶—R¹¹ (wherein A⁶ is —O—, —S—, —SO— or —SO₂—, and R¹¹ is a(C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a phenyl group;a substituted phenyl group having one or more substituents which may bethe same or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; a substituted heterocyclic group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A⁷—R² (wherein A⁷ is a(C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylenegroup, a halo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R¹² is a hydrogen atom; a halogen atom;a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a(C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthiogroup; a halo(C₁-C₆)alkylthio group; a (C₁-C₆)alkylsulfinyl group; ahalo(C₁-C₆)alkylsulfinyl group; a (C₁-C₆)alkylsulfonyl group; ahalo(C₁-C₆)alkylsulfonyl group; a phenyl group; a substituted phenylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aphenoxy group; a substituted phenoxy group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a phenylthio group; a substitutedphenylthio group having one or more substituents which may be the sameor different and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; or a substituted heterocyclic group having one ormore substituents which may be the same or different and are selectedfrom halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups))], and n is an integer of 0 to 3,

X may form a condensed ring by combining together with the adjacentatoms in the heterocyclic ring, and said condensed ring may have one ormore substituents, which may be the same or different, and are selectedfrom halogen atoms; (C₁-C₆)alkyl groups; halo(C₁-C₆)alkyl groups;(C₁-C₆)alkoxy groups; halo(C₁-C₆)alkoxy groups; (C₁-C₆)alkylthio groups;halo(C₁-C₆)alkylthio groups; (C₁-C₆)alkylsulfinyl groups;halo(C₁-C₆)alkylsulfinyl groups; (C₁-C₆)alkylsulfonyl groups;halo(C₁-C₆)alkylsulfonyl groups; phenyl group; substituted phenyl groupshaving one or more substituents which may be the same or different andare selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; heterocyclic groups; and substitutedheterocyclic groups having one or more substituents which may be thesame or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups,

W is O, S or N-R¹³ (wherein R¹³ is a (C₁-C₆)alkyl group; ahalo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenylgroup; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynyl group; a(C₁-C₆)alkoxy group; a phenyl group; a substituted phenyl group havingone or more substituents which may be the same or different and areselected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a phenyl(C₁-C₆)alkyl group; or asubstituted phenyl(C₁-C₆)alkyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups), and p and q, which may be the same ordifferent, are integers of 0 to 1),

B¹, B², B³ and B⁴, which may be the same or different, are carbon atomsor nitrogen atoms,

Y, which may be the same or different, are halogen atoms; cyano groups;nitro groups; halo(C₃-C₆)cycloalkyl groups; phenyl groups; substitutedphenyl groups having one or more substituents which may be the same ordifferent and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups;heterocyclic groups; substituted heterocyclic groups having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A³—R⁸ (wherein A³and R⁸ are asdefined above), and m is an integer of 1 to 5,

Y may form a condensed ring by combining together with the adjacentcarbon atoms in the aromatic ring, and said condensed ring may have oneor more substituents, which may be the same or different, and areselected from halogen atoms; (C₁-C₆)alkyl groups; halo(C₁-C₆)alkylgroups; (C₁-C₆)alkoxy groups; halo(C₁-C₆)alkoxy groups; (C₁-C₆)alkylthiogroups; halo(C₁-C₆)alkylthio groups; (C₁-C₆)alkylsulfinyl groups;halo(C₁-C₆)alkylsulfinyl groups; (C₁-C₆)alkylsulfonyl groups;halo(C₁-C₆)alkylsulfonyl groups; phenyl group; substituted phenyl groupshaving one or more substituents which may be the same or different andare selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; heterocyclic groups; and substitutedheterocyclic groups having one or more substituents which may be thesame or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups, andeach of Z¹ and Z² is an oxygen atom or a sulfur atom,

provided that:

(1) when Het is Q2, Q6, Q7 or Q9 and B¹, B², B³ and B⁴ are carbon atomsat the same time, then Ym is other than 3-chloro-2-methyl group,3-chloro-2,6-diethyl group, 5-chloro-2-methyl group, 2,6-diethyl group,4-chloro-2-fluoro group and 2-ethyl-6-methyl group,

(2) when Het is Q4 and B¹, B², B³ and B⁴ are carbon atoms at the sametime, then Ym is other than 2,5-dichloro group, 2,4-difluoro group,2,6-difluoro group, 3-chloro-2-methyl group, 5-chloro-2-methyl group,5-fluoro-2-methyl group, 2,6-dimethyl group, 2,6-diethyl group,2-ethyl-6-methyl group, 2-methoxy-5-nitro group, 2-methoxy-5-methylgroup, 2,6-diethoxy group, 3-bromo-2-methyl group, 3-fluoro-2-methylgroup, 3-iodo-2-methyl group, 3-cyano-2-methyl group,3-difluoromethoxy-2-methyl group, 5-chloro-2-ethyl group, 2,5-dimethylgroup, 2,3-dichloro group, 3-chloro-2,6-diethyl group, 4-trifluoromethylgroup, 3-methoxycarbonyl-2-methyl group, 3-trifluoromethyl-2-methylgroup, 3,5-dichloro-2,6-diethyl group, 3,4-dichloro group,3-(methoxycarbonylmethyloxy)-2-methyl group, 2-methyl-3-nitro group and4-trifluoromethoxy group,

(3) when Het is Q9, R² and R³ are hydrogen atoms at the same time, Xn isa 2-phenyl group, R¹ is a n-propyl group or an i-propyl group and B¹,B², B³ and B⁴ are carbon atoms at the same time, then Ym is other than4-pentafluoroethyl-2-methyl group, and

(4) when Het is Q10 and B¹, B², B³ and B⁴ are carbon atoms at the sametime, then Ym is other than 5-chloro-2-methyl group, 5-fluoro-2-methylgroup and 2,5-dimethyl group), agricultural and horticulturalinsecticides and their usage.

MODE FOR CARRYING OUT THE INVENTION

In the definition of the general formula (I) for the heterocyclicdicarboxylic acid diamide derivative of the present invention, the term“halogen atom” means a chlorine atom, a bromine atom, an iodine atom ora fluorine atom. The term “(C₁-C₆)alkyl” means a linear or branchedalkyl group of 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl or thelike. The term “halo(C₁-C₆)alkyl” means a substituted linear or branchedalkyl group of 1 to 6 carbon atoms having as the substituent(s) one ormore halogen atoms which may be the same or different. The term “halo(C₃-C₆)cycloalkyl” means a substituted alicyclic hydrocarbon group of 3to 6 carbon atoms having as the substituent(s) one or more halogen atomswhich may be the same or different. The term (C₁-C₈)alkylene means alinear or branched alkylene group of 1 to 8 carbon atoms, such asmethylene, ethylene, propylene, trimethylene, dimethylmethylene,tetramethylene, isobutylene, dimethylethylene, octamethylene or thelike. The term “heterocyclic group” means a heterocyclic group such aspyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group,tetrahydrofuryl group, thienyl group, tetrahydrothienyl group,tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group,isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolylgroup, thiadiazolyl group, imidazolyl group, triazolyl group, pyrazolylgroup or the like. As to the passage “R¹ and R² may form a 4 to 7membered ring by combining to each other, in which the ring may containthe same or different 1 to 3 hetero atoms selected from the groupconsisting of oxygen atom, sulfur atom and nitrogen atom” , the 4 to 7membered ring includes, for example, azetidine ring, pyrrolidine ring,pyrroline ring, piperidine ring, imidazolidine ring, imidazoline ring,oxazolidine ring, thiazolidine ring, isoxazolidine ring, isothiazolidinering, tetrahydropyridine ring, piperazine ring, morpholine ring,thiomorpholine ring, dioxazine ring, dithiazine ring, indole ring,benzo[b]furan ring, benzo[b]thiophene ring, quinoline ring, isoquinolinering, naphthyridine ring and quinoxaline ring.

As to the passage “X may form a condensed ring by combining togetherwith the adjacent atoms in the heterocyclic ring” , the condensed ringrefers to, for example, indole ring, benzo[b]furan ring,benzo[b]thiophene ring, quinoline ring, isoquinoline ring, naphthyridinering, quinoxaline ring or cinnoline ring.

As to the passage “Y may form a condensed ring by combining togetherwith the adjacent carbon atoms in the aromatic ring” , the condensedring refers to a condensed ring such as naphthalene,tetrahydronaphthalene, indene, indan, quinoline, quinazoline, chroman,isochroman, indole, indoline, benzodioxane, benzodioxole, benzofuran,dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzooxazole,benzothiazole, benzoimidazole, indazole or the like.

The heterocyclic dicarboxylic acid diamide derivative of the generalformula (I) of the present invention contains an asymmetric carbon atomor an asymmetric center in the structural formula in some cases, and hasoptical isomers and diastereomers in some cases. The present inventionincludes all of the individual optical isomers and mixtures containingthe optical isomers in any proportions. The heterocyclic dicarboxylicacid diamide derivative of the general formula (I) of the presentinvention has geometrical isomers due to a carbon-carbon double bond ora carbon-nitrogen double bond in the structural formula in some cases.The present invention includes all of the individual geometrical isomersand mixtures containing the geometrical isomers in any proportions.

Preferable compounds as the heterocyclic dicarboxylic acid diamidederivative of the general formula (I) of the present invention are agroup of compounds in which R¹ is a (C₁-C₈)alkyl group, a(C₁-C₆)alkylthio(C₁-C₈)alkyl group, a (C₁-C₆)alkylsulfinyl(C₁-C₈)alkylgroup or a (C₁-C₆)alkyl-sulfonyl(C₁-C₈)alkyl group; R² and R³, which maybe the same or different, are hydrogen atoms or methyl groups; Het is apyridine ring represented by Q1, Q2, Q3 or Q4; X, which may be the sameor different, are halogen atoms, nitro groups, halo(C₁-C₆)alkyl groups,halo(C₁-C₆)alkoxy groups or halo(C₁-C₆)alkylthio groups; n is an integerof 0 to 2; p is an integer of 0 or 1; all of B¹, B², B³ and B⁴ arecarbon atoms, or all of B¹, B² and B⁴are carbon atoms and B³ is anitrogen atom; Y, which may be the same or different, are halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, halo(C₁-C₆)alkoxy groups,halo(C₁-C₆)alkylthio groups or halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkoxygroups; as to the substitution position of Y and the number m ofsubstituents Y, the substitution is di-substitution at the 2- and3-positions or the 2- and 4-positions in relation to the bindingposition of the amide group, or tri-substitution at the 2-, 3- and4-positions or the 2-, 4- and 5-positions in relation to the bindingposition of the amide group; and each of Z¹ and Z² is an oxygen atom.

A group of more preferable compounds are compounds in which R¹ is ani-propyl group, a t-butyl group, a methylthio(C₃-C₄)alkyl group, amethylsulfinyl (C₃-C₄)alkyl group or a methylsulfonyl (C₃-C₆)alkylgroup; each of R² and R³ is a hydrogen atom; Het is a pyridine ringrepresented by Q1, Q2, Q3 or Q4; X is halogen atom; n is an integer of 0to 1; p is an integer of 0 or 1; all of B¹, B², B³ and B⁴ are carbonatoms; Y, which may be the same or different, are chlorine atoms, methylgroups, trifluoromethyl groups, pentafluoroethyl groups,heptafluoropropyl groups, heptafluoroisopropyl groups, trifluoromethoxygroups or 1-trifluoromethyl-2,2,2-trifluoroethoxy groups; as to thesubstitution position of Y and the number m of substituents Y, thesubstitution is di-substitution at the 2- and 4-positions in relation tothe binding position of the amide group; and each of Z¹ and Z² is anoxygen atom.

The heterocyclic dicarboxylic acid diamide derivative of the generalformula (I) of the present invention can be produced, for example, byany of the production processes schematically shown below.

Production Process 1

wherein R¹, R², Het, B¹, B², B³, B⁴, X, Y, m and n are as defined above,hal is a halogen atom, and R is a (C₁-C₃)alkyl group.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-1) can be produced by hydrolyzing a diester of the generalformula (VIII) in the presence of an acid or an alkali to obtain adicarboxylic acid of the general formula (VII), converting saiddicarboxylic acid to an acid anhydride (VI) in the presence of adehydrating agent, reacting the acid anhydride (VI) with a substitutedaromatic amine of the general formula (V) in the presence or absence ofan inert solvent to obtain amides of the general formulas (IV-1) and(IV-2), reacting said amides with a dehydrating agent in the presence orabsence of an inert solvent after or without isolating the amides, toobtain an imide of the general formula (III), and then reacting saidimide with an amine or its salt of the general formula (II-1) or thegeneral formula (II-2), respectively, in the presence or absence of aninert solvent after or without isolating the imide.

(1-1). General Formula (VIII)→General Formula (VII)

As an inert solvent usable in this reaction, there can be used, forexample, water, alcohols (e.g. methanol, ethanol and propanol) aswater-soluble solvents, and mixed solvents of water and water-solublesolvents.

As the base used for the hydrolysis, hydroxides of alkali metals, suchas sodium hydroxide, potassium hydroxide and the like can be used. As tothe amount of the base used, the base may be used in an amount properlychosen in the range of 2 to 10 equivalents per equivalent of the diesterof the general formula (VIII). As the acid, there can be used, forexample, inorganic acids such as hydrochloric acid, sulfuric acid, etc.;and organic acids such as trifluoroacetic acid, etc. The amount of theacid used may be a catalytic amount relative to the diester of thegeneral formula (VIII) and ranges from 0.001 to 0.1 equivalent perequivalent of the diester.

As to the reaction temperature, the reaction can be carried out at roomtemperature or while refluxing the inert solvent used. Although thereaction time is varied depending on the scale of reaction, the reactiontemperature and the like, the reaction may be carried out for a timeproperly chosen in the range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by a recrystallization method, adistillation method, a column chromatographic method, etc., whereby thedesired compound can be produced.

It is also possible to subject the desired compound to the subsequentreaction without isolation after completion of the reaction.

(1-2). General Formula (VII)→General Formula (VI)

As an inert solvent usable in this reaction, any inert solvent may beused so long as it does not markedly inhibit the progress of thereaction. There can be used, for example, halogenated hydrocarbons suchas dichloromethane, chloroform, carbon tetrachloride, etc.; aromatichydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.;acyclic or cyclic ethers such as Methyl Cellosolves, diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran, etc.; and organic acidssuch as acetic acid, trifluoroacetic acid, etc. These inert solvents maybe used singly or as a mixture thereof.

The dehydrating agent may be used in excess to serve also as the inertsolvent.

As the dehydrating agent, there can be used dehydrating agents such asacetic anhydride, trifluoroacetic anhydride, etc. As to the amount ofthese dehydrating agents used, they may be used in an amount properlychosen in the range of 1 mole to excess moles per mole of the compoundof the general formula (VII), and they are preferably used in an amountequimolar with the amount of the compound of the general formula (VII).

The reaction temperature may be properly chosen in the range of roomtemperature to the boiling point of the inert solvent used. When noinert solvent is used, it is sufficient that the reaction is carried outbelow the boiling point of the dehydrating agent used.

Although the reaction time is varied depending on the reactiontemperature, the scale of reaction, and the like, the reaction may becarried out in the range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by a recrystallization method, adistillation method, a column chromatographic method, etc., whereby thedesired compound can be produced.

It is also possible to subject the desired compound to the subsequentreaction without isolation after completion of the reaction.

(1-3). General Formula (VI)→General Formula (IV-1)+General Formula(IV-2)

As the inert solvent usable in this reaction, any inert solvent may beused so long as it does not markedly inhibit the progress of thereaction. There can be exemplified inert solvent including aromatichydrocarbons such as benzene, toluene, xylene, etc.; halogenatedhydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,chlorobenzene, dichlorobenzene, etc.; acyclic or cyclic ethers such asdiethyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethylacetate, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; acids such as acetic acid, etc.; dimethyl sulfoxide;1,3-dimethyl-2-imidazolidinone; and water. These inert solvents may beused singly or as a mixture of two or more thereof.

Since the reaction is an equimolar reaction, it is sufficient that thereactants are used in equimolar amounts, though either of them may beused in excess. If necessary, the reaction may be carried out underdehydrating conditions.

As to the reaction temperature, the reaction can be carried out at roomtemperature or while refluxing the inert solvent used. Although thereaction time is varied depending on the scale of reaction, the reactiontemperature and the like, the reaction may be carried out for a timeproperly chosen in the range of several minutes to 48 hours.

After completion of the reaction, the desired compounds are isolatedfrom the reaction system containing the desired compounds by aconventional method, and if necessary, purified by a recrystallizationmethod, a distillation method, a column chromatographic method, etc.,whereby the desired compounds can be produced.

It is also possible to subject the desired compounds to the subsequentreaction without isolation after completion of the reaction.

(1-4). General Formula (IV-1)+General Formula (IV-2)→General Formula(III)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in (1-2).

It is also possible to subject the desired compounds to the subsequentreaction without isolation after completion of the reaction.

(1-5). General Formula (III)→General Formula (I-1)

As the inert solvent usable in this reaction, pyridines can be usedbesides, for example, the inert solvents exemplified in (1-2).

Since the reaction is an equimolar reaction, it is sufficient that theamine of the general formula (II-1) or the amine salt of the generalformula (II-2) is used in an amount equimolar with the amount of theimide of the general formula (III), though the amine or the amine saltmay be used in excess.

When the amine salt of the general formula (II-2) is used in thereaction, a base is necessary in order to produce free amine in thereaction system. As the base, an inorganic base or an organic base canbe used. The inorganic base includes, for example, hydroxides andcarbonates of alkali metals, such as sodium hydroxide, potassiumhydroxide, sodium carbonate and potassium carbonate. The organic baseincludes, for example, triethylamine, pyridine,4-(dimethylamino)pyridine and 1,8-diazabicyclo[5.4.0]-7-undecene. As tothe amount of these bases used, they may be used in an amount properlychosen in the range of 1 mole to excess moles per mole of the amine saltof the general formula (II-2).

The reaction temperature may be properly chosen in the range of −10° C.to the boiling point of the inert solvent used, and the reaction ispreferably carried out in the range of 0° C. to 150° C.

Although the reaction time is varied depending on the reactiontemperature, the scale of reaction, and the like, the reaction may becarried out in the range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by a recrystallization method, adistillation method, a column-chromatographic method, etc., whereby thedesired compound can be produced.

The compound of the general formula (VIII), i.e., the starting materialin the reaction can be produced according to a well-known process, forexample, the processes described in, for instance, J. Am. Chem. Soc.,63, 1762 (1941), J. Heterocyclic Chem., 21, 1431 (1984), J. Indian Chem.Soc., 1982, 1372, J. Org. Chem., 14, 723 (1949), Heterocycles, 27, 1489(1988), J. Am. Chem. Soc., 78, 2220 (1956), J. Prakt. Chem., 311, 807(1969), Tetrahedron, 36, 1801 (1980), JP-A-6-122684, U.S. Pat. No.3,414,580, ditto 3,686,171, J. Med. Chem., 27, 1396 (1984), J.Heterocyclic Chem., 12, 1303 (1975)., ditto 15, 1477 (1978), ditto 16,1141 (1979), ditto 17, 443 (1982), ditto 21, 689 (1984), Beil., 25III,2028, JP-A-52-77086, J. Am. Chem. Soc., 81, 2456 (1956), J. Org. Chem.,37, 3224 (1972), JP-A-62-175480, JP-A-62-230782, JP-A-60-69083,JP-A-60-185783, JP-A-61-109790, JP-A-62-277385, JP-A-63-295575,JP-A-63-99067, JP-A-64-75474, JP-A-64-90118, Yakugaku Zasshi, 84, 416(1964), Chem. and Pharm. Bull., 5, 277 (1957), Chem. Research (S), 1989,196, Chem. Pharm. Bull., 2, (7), 1513 (1972), J. Heterocyclic Chem., 27,579 (1990), Tetrahedron, 53 (42), 14497 (1997), ditto 41 (7), 1199(1985), Chem. Ber., 107, 3036 (1974), J. Heterocyclic Chem., 23, 1103(1986), ditto 5, 125 (1968), J. Org. Chem., 26, 468 (1961), etc.

Production Process 2

wherein R¹, R², Het, B¹, B², B³, B⁴, X, Y, hal, m and n are as definedabove, and X′ is a halogen atom or a nitro group, provided that X isother than hydrogen atom and nitro group.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-1) can be produced by reacting a heterocyclic dicarboxylicacid imide derivative of the general formula (III-1) with a reactantcorresponding to X, in the presence of an inert solvent to obtain aheterocyclic dicarboxylic acid imide derivative of the general formula(III), and reacting said heterocyclic dicarboxylic acid imide derivative(III) with an amine or its salt of the general formula (II-1) or thegeneral formula (II-2), respectively, after or without isolating thederivative (III).

(2-1). General Formula (III-1)→General Formula (III)

In the case of this reaction, the production can be carried outaccording to the process described in J. Org. Chem., 42, 3415 (1977),Tetrahedron, 25, 5921 (1969), Synthesis, 1984, 667, Chem. Lett., 1973,471, J. Org. Chem., 39, 3318 (1974), ditto 39, 3327 (1974), etc.

(2-2). General Formula (III)→General Formula (I-1)

In the case of this reaction, the production can be carried outaccording to production process (1-5).

Production Process 3

wherein R¹, R², Het, B¹, B², B³, B⁴, X, Y, hal, m and n are as definedabove.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-1) can be produced by reacting a heterocyclic dicarboxylicacid anhydride derivative of the general formula (VI-1) with an aromaticamine of the general formula (V) in the presence of an inert solvent toobtain amides of the general formulas (IV-1′) and (IV-2′), reacting saidamides with a dehydrating agent in the presence or absence of an inertsolvent after or without isolating the amides, to obtain a heterocyclicdicarboxylic acid imide derivative of the general formula (III-2),subjecting said heterocyclic dicarboxylic acid imide derivative (III-2)to catalytic reduction with hydrogen after or without isolation toobtain a heterocyclic dicarboxylic acid imide derivative of the generalformula (III-3), diazotizing said heterocyclic dicarboxylic acid imidederivative (III-3) after or without isolation, adding a metal saltthereto to obtain a heterocyclic dicarboxylic acid imide derivative ofthe general formula (III), and then reacting said heterocyclicdicarboxylic acid imide derivative (III) with an amine or its salt ofthe general formula (II-1) or the general formula (II-2), respectively,after or without isolating the derivative (III).

(3-1). General Formula (VI-1)→General Formula (IV-1′)+General Formula(IV-2′)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (1-3).

(3-2). General Formula (IV-1′)+General Formula (IV-2′)→General Formula(III-2)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (1-4).

(3-3). General Formula (III-2)→General Formula (III-3)

As an inert solvent usable in this reaction, any inert solvent may beused so long as it does not markedly inhibit the progress of thereaction. There can be exemplified alcohols such as methanol, ethanol,propanol, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane,tetrahydrofuran, etc.; and acids such as acetic acid, etc. These inertsolvents may be used singly or as a mixture of two or more thereof.

As a catalyst for the catalytic reduction used in the reaction, therecan be exemplified palladium-carbon, Raney nickel, palladium black andplatinum black. As to the amount of the catalyst used, the catalyst maybe used in an amount properly chosen in the range of 0.1 to 10 wt %based on the weight of the heterocyclic dicarboxylic acid imidederivative of the general formula (III-2). The reaction is carried outunder a hydrogen atmosphere, and the reaction may be carried out at ahydrogen pressure properly chosen in the range of 1 to 10 atmosphericpressure.

As to the reaction temperature, the reaction may be carried out at roomtemperature to the reflux temperature of the inert solvent used.Although the reaction time is varied depending on the scale of reaction,the reaction temperature and the like, it may be properly chosen in therange of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced. Itis also possible to subject the desired compound to the subsequentreaction without isolation from the reaction system.

(3-4). General Formula (III-3)→General Formula (III)

As an inert solvent used in this reaction, acidic solvents can be used.There can be exemplified an aqueous hydrochloric acid solution, anaqueous hydrobromic acid solution, an aqueous hydroiodic acid solution,an aqueous sulfuric acid solution, acetic acid and trifluoroacetic acid.These acidic solvents may be used singly or as a mixture of two or morethereof. In addition, these acidic solvents may be used in admixturewith ethers such as tetrahydrofuran, dioxane, etc.

As a diazotizing agent, there can be exemplified diazotizing agents suchas sodium nitrite, nitrosyl hydrogensulfate, alkyl nitrites, etc. As tothe amount of these diazotizing agents used, the reaction may be carriedout by properly choosing the amount in the range of an amount equal tothat of the heterocyclic dicarboxylic acid imide derivative of thegeneral formula (III-3) to an excess amount over this derivative.

As to the reaction temperature, the reaction may be carried out at −50°C. to room temperature or at the reflux temperature of the inert solventused. Although the reaction time is varied depending on the scale ofreaction, the reaction temperature and the like, it may be properlychosen in the range of several minutes to 48 hours.

As the metal salt added after the production of the diazonium salt,there can be used metal salts such as cuprous chloride, cuprous bromide,potassium iodide, copper cyanide, potassium xanthate, mercaptan sodium,etc. As to the amount of the metal salt used, the reaction may becarried out by properly choosing the amount in the range of 1 equivalentto excess equivalents per equivalent of the heterocyclic dicarboxylicacid imide derivative of the general formula (III-3).

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced. Itis also possible to subject the desired compound to the subsequentreaction without isolation from the reaction system.

In the case of the reaction, the production can be carried out accordingto the process described in Org. Synth., IV, 160 (1963), ditto III, 809(1959), J. Am. Chem. Soc., 92, 3520 (1970), etc.

C. (3-5). General Formula (III)→General Formula (I-1)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (1-5).

Production Process 4

wherein R¹, R², Het, B¹, B², B³, B⁴, X, Y, hal, m and n are as definedabove.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-1) can be produced by reacting a heterocyclic dicarboxylicacid imide derivative of the general formula (III-2) with an amine orits salt of the general formula (II-1) or the general formula (II-2),respectively, in the presence of an inert solvent to obtain aheterocyclic dicarboxylic acid diamide derivative of the general formula(I-3), subjecting said heterocyclic dicarboxylic acid diamide derivative(I-3) to catalytic reduction with hydrogen after or without isolation toobtain a heterocyclic dicarboxylic acid diamide derivative of thegeneral formula (I-2), diazotizing said heterocyclic dicarboxylic aciddiamide derivative (I-2) after or without isolation, and then adding ametal salt thereto.

(4-1). General Formula (III-2)→General Formula (I-3)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (1-5).

(4-2). General Formula (I-3)→General Formula (I-2)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (3-3).

(4-3). General Formula (I-2)→General Formula (I-1)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (3-4).

Production Process 5

wherein R¹, R², R³, Het, B¹, B², B³, B⁴, X, Y, m and n are as definedabove.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-5) or the general formula (I-4) can be produced by reacting aheterocyclic dicarboxylic acid anhydride of the general formula (VI)with an amine or its salt of the general formula (II-1) or the generalformula (II-2), respectively, in the presence of an inert solvent toobtain a heterocyclic dicarboxylic acid amide of the general formula(IV-3), and treating said heterocyclic dicarboxylic acid amide after orwithout isolation as follows: when its R² is a hydrogen atom, theheterocyclic dicarboxylic acid amide (IV-3) is subjected to condensationreaction in the presence of a condensing agent to obtain a compound ofthe general formula (IX), and said compound (IX) is reacted with anaromatic amine of the general formula (V-1) in the presence of an inertsolvent after or without isolating the compound (IX); or when its R² isother than a hydrogen atom, the heterocyclic dicarboxylic acid amide(IV-3) is condensed with an aromatic amine of the general formula (V-1)in the presence of a condensing agent.

Alternatively, a heterocyclic dicarboxylic acid diamide derivative ofthe general formula (I-1) or the general formula (I-4) can be producedby reacting a heterocyclic dicarboxylic acid anhydride of the generalformula (VI) with an aromatic amine of the general formula (V-1) in thepresence of an inert solvent to obtain a heterocyclic dicarboxylic acidamide of the general formula (IV-4), and treating said heterocyclicdicarboxylic acid amide (IV-4) after or without isolation as follows:when its R³ is a hydrogen atom, the heterocyclic dicarboxylic acid amide(IV-4) is subjected to condensation reaction in the presence of acondensing agent to obtain a compound of the general formula (IX-1), andsaid compound (IX-1) is reacted with an amine or its salt of the generalformula (II-1) or the general formula (II-2), respectively, in thepresence of an inert solvent after or without isolating the compound(IX-1); or when its R³ is other than a hydrogen atom, the heterocyclicdicarboxylic acid amide (IV-4) is condensed with an amine or its salt ofthe general formula (II-1) or the general formula (II-2), respectively,in the presence of a condensing agent.

(5-1). General Formula (VI)→General Formula (IV-3) or General Formula(IV-4)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (1-3).

(5-2). General Formula (IV-3)→General Formula (IX) or General Formula(IV-4)→General Formula (IX-1)

In the case of this reaction, the desired compound can be producedaccording to the process described in J. Med. Chem., 10, 982 (1967).

(5-3). General Formula (IV-3) or General Formula (IV-4)→General Formula(I-4)

The production can be carried out by reacting a heterocyclicdicarboxylic acid amide derivative of the general formula (IV-3) or thegeneral formula (IV-4) with an amine of the general formula (II-1) or(II-2) or the general formula (V-1) in the presence of a condensingagent and an inert solvent. It is also possible to carry out thereaction in the presence of a base if necessary.

The inert solvent used in the reaction includes, for example,tetrahydrofuran, diethyl ether, dioxane, chloroform and dichloromethane.As the condensing agent used in the reaction, any condensing agent maybe used so long as it is used in conventional amide synthesis. Thecondensing agent includes, for example, Mukaiyama reagent(2-chloro-N-methylpyridinium iodide), DCC(1,3-dicyclohexylcarbodiimide), CDI (carbonyl diumidazole) and DEPC(diethyl cyanophosphonate). As to the amount of the condensing agentused, the condensing agent may be used in an amount properly chosen inthe range of 1 mole to excess moles per mole of the heterocyclicdicarboxylic acid amide derivative of the general formula (IV-3) or thegeneral formula (IV-4).

The base usable in the reaction includes, for example, organic basessuch as triethylamine, pyridine, etc.; and inorganic bases such aspotassium carbonate. As to the amount of the base used, the base may beused in an amount properly chosen in the range of 1 mole to excess molesper mole of the heterocyclic dicarboxylic acid amide derivative of thegeneral formula (IV-3) or the general formula (IV-4).

As to the reaction temperature, the reaction may be carried out at 0° C.to the boiling point of the inert solvent used. Although the reactiontime is varied depending on the scale of reaction, the reactiontemperature and the like, it ranges from several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced.

(5-4). General Formula (IX)→General Formula (I-5) or General Formula(IX-1)→General Formula (I-1)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (1-5).

Production Process 6

wherein R, R¹, R², Het, B¹, B², B³, B⁴, X, Y, hal, m and n are asdefined above.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-1) can be produced by halogenating a heterocyclicdicarboxylic acid ester derivative of the general formula (X) in thepresence or absence of an inert solvent to obtain a heterocyclicdicarboxylic acid halide of the general formula (XI), reacting saidheterocyclic dicarboxylic acid halide (XI) with an aromatic amine of thegeneral formula (V) in the presence of an inert solvent and a base afteror without isolating the halide (XI), to obtain a heterocyclicdicarboxylic acid amide of the general formula (IV-3), hydrolyzing saidheterocyclic dicarboxylic acid amide (IV-3) in the presence or absenceof an inert solvent after or without isolating the amide (IV-3), toobtain a heterocyclic dicarboxylic acid amide of the general formula(IV-1), subjecting said heterocyclic dicarboxylic acid amide (IV-1) tocondensation reaction after or without isolation to obtain aheterocyclic dicarboxylic acid isoimide derivative of the generalformula (IX-1), reacting said heterocyclic dicarboxylic acid isoimidederivative (IX-1) with an amine or its salt of the general formula(II-1) or the general formula (II-2), respectively.

(6-1). General Formula (X)→General Formula (XI)

As the inert solvent usable in this reaction, any inert solvent may beused so long as it does not markedly inhibit the progress of thereaction. There can be exemplified inert solvents including aromatichydrocarbons such as benzene, toluene, xylene, etc.; halogenatedhydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,etc.; chlorinated aromatic hydrocarbons such as chlorobenzene,dichlorobenzene, etc.; acyclic or cyclic ethers such as diethyl ether,dioxane, tetrahydrofuran, etc.; and esters such as ethyl acetate, etc.These inert solvents may be used singly or as a mixture of two or morethereof.

As a halogenating agent, there can be used halogenating agents such asthionyl chloride, phosphorus oxychloride, phosphorus trichloride, etc.As to the amount of the halogenating agent used, the halogenating agentmay be used in an amount properly chosen in the range of 1 to 10equivalents per equivalent of the heterocyclic dicarboxylic acid esterderivative of the general formula (X).

As to the reaction temperature, the reaction may be carried out at 0° C.to the reflux temperature of the inert solvent used. Although thereaction time is varied depending on the scale of reaction, the reactiontemperature and the like, it may be properly chosen in the range ofseveral minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced. Itis also possible to subject the desired compound to the subsequentreaction without isolation from the reaction system.

(6-2). General Formula (XI)→General Formula (IV-3)

As the inert solvent usable in this reaction, there can be used, forexample, the inert solvents exemplified in production process (1-3).

As the base, an inorganic base or an organic base can be used. As theinorganic base, there can be used, for example, hydroxides of alkalimetals, such as sodium hydroxide, potassium hydroxide, etc. As theorganic base, organic bases such as triethylamine, pyridine and the likecan be used. As to the amount of the base used, the base may be used inan amount properly chosen in the range of 0.5 to 3 equivalents perequivalent of the heterocyclic dicarboxylic acid halide of the generalformula (XI).

Since the reaction is an equimolar reaction, it is sufficient that thereactants are used in equimolar amounts, though the reaction may becarried out by properly choosing the amount of the aromatic amine of thegeneral formula (V) in the range of 0.5 to 2 equivalents per equivalentof the aromatic dicarboxylic acid halide of the general formula (XI).

As to the reaction temperature, the reaction may be carried out at 0° C.to the reflux temperature of the inert solvent used. Although thereaction time is varied depending on the scale of reaction, the reactiontemperature and the like, it may be properly chosen in the range ofseveral minutes to 48 hours.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced. Itis also possible to subject the desired compound to the subsequentreaction without isolation from the reaction system.

(6-3). General Formula (IV-3)→General Formula (IV-1)

In the case of this reaction, the desired compound can be producedaccording to production process (1-1).

(6-4). General Formula (IV-1)→General Formula (IX-1)

In the case of this reaction, the desired compound can be producedaccording to production process (5-2).

(6-5). General Formula (IX-1)→General Formula (I-1)

In the case of this reaction, the desired compound can be producedaccording to production process (I-5).

Production Process 7

wherein R¹, R², Het, B¹, B², B³, B⁴, X, Y, hal, m and n are as definedabove.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-1) can be produced by halogenating a heterocyclicdicarboxylic acid of the general formula (VII) in the presence of ahalogenating agent to obtain an acid halide of the general formula(XII), reacting said acid halide (XII) with a substituted aromatic amineof the general formula (V) in the presence or absence of an inertsolvent to obtain a heterocyclic dicarboxylic acid isoimide and aheterocyclic dicarboxylic acid imide of the general formulas (IX-1) and(III), respectively, and reacting these compounds with an amine or itssalt of the general formula (II-1) or the general formula (II-2),respectively, in the presence or absence of an inert go solvent after orwithout isolating said compounds.

(7-1). General Formula (VII)→General Formula (XII)

In the case of this reaction, the desired compound can be producedaccording to production process (6-1).

(7-2). General Formula (XII)→General Formulas (IX-1) and (III)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (6-2).

(7-3). General Formulas (IX-1) and (III)→General Formula (I-1)

In the case of this reaction, the desired compound can be produced in amanner similar to that described in production process (1-5).

Production Process 8

wherein R¹, R², Het, B¹, B², B³, B⁴, X, Y, hal, m and n are as definedabove.

A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-1), (I-4) or (1-5) can be produced by subjecting aheterocyclic carboxylic acid amide of the general formula (XIII-1) orthe general formula (XIII-2) to ortho-metallation by the use of a metalreagent such as butyllithium, reacting the ortho-metallation productwith carbon dioxide to obtain a heterocyclic dicarboxylic acid amidederivative of the general formula (IV-3) or the general formula (IV-4),and treating this derivative in the same manner as in productionprocesses (5-2) to (5-4).

(8-1). General Formula (XIII-1) or General Formula (XIII-2)→GeneralFormula (IV-3) or General Formula (IV-4)

In the case of this reaction, the production can be carried out bylithiation at the ortho-position according to the method described in J.Org. Chem., 29, 853 (1964) and then introducing carbon dioxide toreplace the lithium therewith at −80° C. to room temperature.

After completion of the reaction, the desired compound is isolated fromthe reaction system containing the desired compound by a conventionalmethod, and if necessary, purified by recrystallization, columnchromatography, etc., whereby the desired compound can be produced.

Production Process 9

wherein R¹, R², Het, X, Y, hal, m and n are as defined above.

The reaction is oxidation of the nitrogen atom in the heterocyclic ring.A heterocyclic dicarboxylic acid diamide derivative of the generalformula (I-6) can be produced by reacting a heterocyclic dicarboxylicacid imide of the general formula (III-4) with an oxidizing agent in thepresence of an inert solvent to obtain a heterocyclic dicarboxylic acidimide derivative of the general formula (III-5), and reacting saidheterocyclic dicarboxylic acid imide derivative (III-5) with an amine orits salt of the general formula (II-1) or the general formula (II-2),respectively, after or without isolating the derivative (III-5).

(9-1). General Formula (III-4)→General Formula (III-5)

As the inert solvent usable in this reaction, any inert solvent may beused so long as it does not inhibit the progress of the reaction. Therecan be exemplified dichloromethane, chloroform, carbon tetrachloride,chlorobenzene, water, acetic acid, ethyl acetate and trifluoroaceticacid. These inert solvents may be used singly or as a mixture of two ormore thereof.

As the oxidizing agent used in the reaction, hydrogen peroxide,m-chloroperbenzoic acid and peracetic acid can be exemplified.

As to the reaction temperature for said reaction, the reaction may becarried out at 0° C. to 100° C. Although the reaction time is varieddepending on the scale of reaction, the reaction temperature and thelike, it may be properly chosen in the range of several minutes to 48hours.

(9-2). General Formula (III-5)→General Formula (I-6)

In the case of this reaction, the production can be carried outaccording to production process (I-5).

Typical examples of the heterocyclic dicarboxylic acid diamidederivative of the general formula (I) of the present invention are givenin Tables 1 to 33 but they are not intended in any way to limit thescope of the present invention.

General Formula (I)

 

TABLE 1 (Z¹ = Z² = O, R³ = H, Het = Q1, B¹ = B² = B³ = B⁴ = C) Physicalproperty No R¹ R² p Xn Ym m.p. ° C.  1 H H 0 H 2-CH₃-4-CF₂CF₃  2 CH₃ H 0H 4-CF₃  3 CH₃ H 0 H 2-CH₃-4-Cl  4 CH₃ H 0 H 2-CH₃-4-OCHF₂  5 CH₃ H 0 H2-CH₃-4-CF₂CF₃  6 CH₃ H 0 H 2-CH₃-4-OCF₃  7 C₂H₅ H 0 H 2-CH₃-4-CF₃  8C₂H₅ H 0 H 2-CH₃-4-OCHF₂  9 C₂H₅ H 0 H 2-CH₃-4-OCF₃  10 C₂H₅ H 0 H2-CH₃-4-CF₂CF₃  11 C₂H₅ H 0 H 2-CH₃-4-CF(CF₃)₂  12 C₂H₅ C₂H₅ 0 H2-CH₃-4-CF₂CF₃ 108-111  13 C₂H₅ C₂H₅ 0 4-Cl 2-CH₃-4-CF₂CF₃ 111-114  14n-C₃H₇ H 0 H 2-CH₃-4-CF(CF₃)₂  15 n-C₃H₇ H 0 H 4-CF₃  16 n-C₃H₇ H 0 H2-CH₃-4-OCF₃  17 n-C₃H₇ H 0 H 2-CH₃-4-CF₂CF₃  18 C(CH₃)₂CH₂ H 0 H2-CH₃-4-CF(CF₃)₂ 64-65 —SCH₃ H 0 H 2-CH₃-4-CF(CF₂)₂  19 n-C₃H₇ H 0 H2-Cl-4-CF(CF₃)₂  20 i-C₃H₇ H 0 H 4-CF₃  21 i-C₃H₇ H 0 H 2-NO₂  22 i-C₃H₇H 0 H 4-NO₂  23 i-C₃H₇ H 0 H 4-F  24 i-C₃H₇ H 0 H 2-CH₃  25 i-C₃H₇ H 0 H4-CF₃  26 i-C₃H₇ H 0 H 3-CF₃  27 i-C₃H₇ H 0 H 4-CF₂CF₂CF₃  28 i-C₃H₇ H 0H 4-(CF₂)₃CF₃  29 i-C₃H₇ H 0 H 4-OCF₃  30 i-C₃H₇ H 0 H 4-OCF₂CHFOC₃F₇-n 31 i-C₃H₇ H 0 H 3-SCF₃  32 CH(CH₃)CH₂SCH₃ H 0 H 2-CH₃-4-CF(CF₃)₂ paste 33 i-C₃H₇ H 0 H 4-SCH₂CF₃  34 i-C₃H₇ H 0 H 4-SCF₂CHF₂  35 i-C₃H₇ H 0 H4-S(CF₂)₃CF₃  36 i-C₃H₇ H 0 H 4-SCF(CF₃)₂  37 i-C₃H₇ H 0 H 4-SCF₂CBrF₂ 38 i-C₃H₇ H 0 H 4-SOCF₂CBrF₂  39 i-C₃H₇ H 0 H 4-SO(CF₂)₃CF₃  40 i-C₃H₇H 0 H 4-SO₂CH₂CF₃  41 i-C₃H₇ H 0 H 2,3-Cl₂  42 i-C₃H₇ H 0 H 2,4-Cl₂  43i-C₃H₇ H 0 H 3,4-F₂  44 i-C₃H₇ H 0 H 2,4-(CH₃)₂  45 i-C₃H₇ H 0 H2-Cl-4-CF₃  46 i-C₃H₇ H 0 H 2-Cl-4-CF(CF₃)₂  47 i-C₃H₇ H 0 H 2-Cl-4-OCF₃ 48 i-C₃H₇ H 0 H 2-Br-4-OCF₃  49 i-C₃H₇ H 0 H 2-CH₃-3-Cl  50 i-C₃H₇ H 0H 2-CH₃-4-Cl  51 i-C₃H₇ H 0 H 2-CH₃-5-Cl  52 i-C₃H₇ H 0 H 2-CH₃-4-Br  53i-C₃H₇ H 0 H 2-CH₃-5-F  54 i-C₃H₇ H 0 H 2-CH₃-4-CF₃ 167-169  55 i-C₃H₇ H0 H 2-CH₃-4-CF₂CF₃ 188-189  56 i-C₃H₇ H 0 H 2-CH₃-4-CF₂CF₂CF₃  57 i-C₃H₇H 0 H 2-CH₃-4-CF(CF₃)₂ 134-136  58 i-C₃H₇ H 1 H 2-CH₃-4-CF(CF₃)₂  59i-C₃H₇ H 0 H 2-CH₃-4-OCF₃  60 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CHF₂  61 i-C₃H₇ H0 H 2-CH₃-3-OCF₂CHClF  62 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CHClF  63 i-C₃H₇ H 0H 2-CH₃-4-CF₂CBrF₂  64 i-C₃H₇ H 0 H 2-CH₃-4-CF₂CCl₂F  65 i-C₃H₇ H 0 H2-CH₃-4-OCF₂CHFCF₃  66 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CBrFCF₃  67 i-C₃H₇ H 0 H2-CH₃-4-OCF₂CHFOCF₃  68 i-C₃H₇ H 0 H 2-CH₃-4-SC₃H₇-i  69 i-C₃H₇ H 0 H2-CH₃-4-OCH₂OCH₃  70 i-C₃H₇ H 0 H 2-CH₃-4-OCH₂SCH₃  71 i-C₃H₇ H 0 H2-CH₃-4-COOCH₃  72 i-C₃H₇ H 0 H 2-CH₃-4-OCH₂COOCH₃  73 i-C₃H₇ H 0 H2-CH₃-4-(F₅—PhO)  74 i-C₃H₇ H 0 H 2-CH₃-4-(3-CF₃—PhO)  75 i-C₃H₇ H 0 H2-CH₃-4-(2-Cl-4-CF₃—PhO)  76 i-C₃H₇ H 0 H 2-CH₃-4-(4-Cl-Ph—CH₂O)  77i-C₃H₇ H 0 H 2-CH₃-4-(4-Cl—PhS)  78 i-C₃H₇ H 0 H 2-CH₃-4-(5-CF₃-2-Pyr—O) 79 i-C₃H₇ H 0 H 2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O)  80 i-C₃H₇ H 0 H4-(3-Cl-5-CF₃-2-Pyr—S)  81 i-C₃H₇ H 0 H 2-CH₃-4-P═O(OC₂H₅)₂  82 i-C₃H₇ H0 H 2-CH₃-4-OP═S(OCH₃)₂  83 i-C₃H₇ H 0 H 2-CF₃-4-OCHF₂  84 i-C₃H₇ H 0 H3,5-Cl₂-4-OCHF₂  85 i-C₃H₇ H 0 H 3-N═C(CF₃)—NH-4  86 i-C₃H₇ H 0 H3-N═C(CF₃)—N(CH₃)-4  87 i-C₃H₇ H 0 4-Cl 4-C₄H₉-n  88 i-C₃H₇ H 0 4-Cl4-C₄H₉-t  89 i-C₃H₇ H 0 4-Cl 4-CF(CF₃)₂  90 i-C₃H₇ H 0 4-Cl 4-CF₂CF₂CF₃ 91 i-C₃H₇ H 0 4-Cl 4-(CF₂)₃CF₃  92 i-C₃H₇ H 0 4-Cl 4-OCHF₂  93 i-C₃H₇ H0 4-Cl 4-OCF₂CHFOC₃F₇-n  94 i-C₃H₇ H 0 4-Cl 4-SCH₃  95 i-C₃H₇ H 0 4-Cl4-SOCH₃  96 i-C₃H₇ H 0 4-Cl 4-SO₂CH₃  97 i-C₃H₇ H 0 4-Cl 4-SCHF₂  98i-C₃H₇ H 0 4-Cl 3-SCF₃  99 i-C₃H₇ H 0 4-Cl 3-SOCF₃ 100 i-C₃H₇ H 0 4-Cl4-SCH₂CF₃ 101 i-C₃H₇ H 0 4-Cl 4-SCF₂CHF₂ 102 i-C₃H₇ H 0 4-Cl 4-SCF₂CBrF₂103 i-C₃H₇ H 0 4-Cl 4-SCF(CF₃)₂ 104 i-C₃H₇ H 0 4-Cl 4-S(CF₂)₃CF₃ 105i-C₃H₇ H 0 4-Cl 4-SOCF(CF₃)₂ 106 i-C₃H₇ H 0 4-Cl 4-SO₂CH₂CF₃ 107 i-C₃H₇H 0 4-Cl 4-SO₂CF₂CHF₂ 108 i-C₃H₇ H 0 4-Cl 4-COCH₃ 109 i-C₃H₇ H 0 4-Cl4-Ph 110 i-C₃H₇ H 0 4-Cl 2,3-Cl₂ 111 i-C₃H₇ H 0 4-Cl 2,4-Cl₂ 112 i-C₃H₇H 0 4-Cl 2,4-F₂ 113 i-C₃H₇ H 0 4-Cl 2-Cl-4-F 114 i-C₃H₇ H 0 4-Cl2-F-4-Cl 115 i-C₃H₇ H 0 4-Cl 2,3,4-F₃ 116 i-C₃H₇ H 0 4-Cl 2,3-(CH₃)₂ 117i-C₃H₇ H 0 4-Cl 2-CH₃-3-Cl 118 i-C₃H₇ H 0 4-Cl 2-CH₃-4-Cl 119 i-C₃H₇ H 04-Cl 2-CH₃-5-Cl 120 i-C₃H₇ H 0 4-Cl 2-CH₃-4-Br 121 i-C₃H₇ H 0 4-Cl2-CH₃-4-I 122 i-C₃H₇ H 0 4-Cl 2-CH₃-4-OCH₃ 123 i-C₃H₇ H 0 4-Cl2,3-(CH₃)₂-4-OCH₃ 124 i-C₃H₇ H 0 4-Cl 2-Cl-4-CF₃ 125 i-C₃H₇ H 1 4-Cl2-Cl-4-CF(CF₃)₂ 126 i-C₃H₇ H 0 4-Cl 2-CH₃-4-CF₃ 127 i-C₃H₇ H 0 4-Cl2-CH₃-4-CF₂CF₃ 162-167 128 i-C₃H₇ H 0 4-Cl 2-CH₃-4-OCF₂CCl₃ 129 i-C₃H₇ H0 4-Cl 2-CH₃-4-CF₂CF₂CF₃ 130 i-C₃H₇ H 0 4-Cl 2-CH₃-4-CF(CF₃)₂ 131 i-C₃H₇H 0 4-Cl 2-CH₃-4-(CF₂)₃CF₃ 132 s-C₄H₉ H 0 4-Cl 2-CH₃-4-(CF₂)₃CF₃ 133i-C₄H₉ H 0 4-Cl 2-CH₃-4-CF(CF₃)₂ 134 t-C₄H₉ H 0 4-Cl 2-Cl-4-OCF₃ 135t-C₄H₉ H 0 4-Cl 2-Br-4-OCF₃ 136 t-C₄H₉ H 0 4-Cl 2-CH₃-4-CF₂CF₃ 175-180137 i-C₃H₇ H 0 4-Br 2-Cl-4-CF₃ 138 i-C₃H₇ H 0 4-Br 2-Cl-4-CF(CF₃)₂ 139i-C₃H₇ H 0 4-Br 2-CH₃-4-CF₃ 140 i-C₃H₇ H 0 4-Br 2-CH₃-4-CF₂CF₃ 141i-C₃H₇ H 0 4-Br 2-CH₃-4-OCF₂CCl₂ 142 i-C₃H₇ H 0 4-Br 2-CH₃-4-CF₂CF₂CF₃143 i-C₃H₇ H 0 4-Br 2-CH₃-4-CF(CF₃)₂ 144 i-C₃H₇ H 0 4-Br2-CH₃-4-(CF₂)₃CF₃ 145 i-C₃H₇ H 0 4-Br 2-CH₃-4-(CF₂)₅CF₃ 146 i-C₃H₇ H 04-Br 3-Cl-4-OCHF₂ 147 i-C₃H₇ H 0 4-Br 2-Cl-4-OCF₃ 148 i-C₃H₇ H 0 4-Br2-Br-4-OCF₃ 149 i-C₃H₇ H 0 4-Br 2-Br-4-CF(CF₃)₂ 150 i-C₃H₇ H 0 4-I2-CH₃-3-Cl 151 i-C₃H₇ H 0 4-I 2-CH₃-4-Cl 152 i-C₃H₇ H 0 4-I 2-CH₃-5-Cl153 i-C₃H₇ H 0 4-I 2-CH₃-4-Br 154 i-C₃H₇ H 0 4-I 2-CH₃-4-I 155 i-C₃H₇ H0 4-I 2-CH₃-4-OCH₃ 156 i-C₃H₇ H 0 4-I 2,3-(CH₃)₂-4-OCH₃ 157 i-C₃H₇ H 04-I 2-Cl-4-CF₃ 158 i-C₃H₇ H 0 4-I 2-Cl-4-CF(CF₃)₂ 159 i-C₃H₇ H 0 4-I2-CH₃-4-CF₂CF₃ 160 i-C₃H₇ H 1 4-I 2-CH₃-4-CF₂CF₃ 161 i-C₃H₇ H 0 4-I2-CH₃-4-OCF₂CCl₃ 162 i-C₃H₇ H 0 4-I 2-CH₃-4-CF₂CF₂CF₃ 163 i-C₃H₇ H 0 4-I2-CH₃-4-CF(CF₃)₂ 164 i-C₃H₇ H 0 4-I 2-CH₃-4-(CF₂)₃CF₃ 165 i-C₃H₇ H 0 4-I2-CH₃-4-(CF₂)₅CF₃ 166 i-C₃H₇ H 0 4-I 3-Cl-4-OCHF₂ 167 i-C₃H₇ H 0 4-I2-Cl-4-OCF₃ 168 i-C₃H₇ H 0 4-I 2-Br-4-OCF₃ 169 i-C₃H₇ H 0 4-I2-Br-4-CF(CF₃)₂ 170 i-C₃H₇ H 0 6-Cl 2-CH₃-3-Cl 171 i-C₃H₇ H 0 6-Cl2-CH₃-4-Cl 172 i-C₃H₇ H 0 6-Cl 2-CH₃-5-Cl 173 i-C₃H₇ H 0 6-Cl 2-CH₃-4-Br174 i-C₃H₇ H 0 6-Cl 2-CH₃-4-I 175 i-C₃H₇ H 0 6-Cl 2-CH₃-4-OCH₃ 176i-C₃H₇ H 0 6-Cl 2,3-(CH₃)₂-4-OCH₃ 177 i-C₃H₇ H 0 6-Cl 2-Cl-4-CF₃ 178i-C₃H₇ H 0 6-Cl 2-Cl-4-CF(CF₃)₂ 179 i-C₃H₇ H 0 6-Cl 2-CH₃-4-CF₃ 180i-C₃H₇ H 0 6-Cl 2-CH₃-4-CF₂CF₃ 181 i-C₃H₇ H 0 6-Cl 2-CH₃-4-OCF₂CCl₃ 182i-C₃H₇ H 0 6-Cl 2-CH₃-4-CF₂CF₂CF₃ 183 i-C₃H₇ H 0 6-Cl 2-CH₃-4-CF(CF₃)₂184 i-C₃H₇ H 0 6-Cl 2-CH₃-4-(CF₂)₃CF₃ 185 i-C₃H₇ H 0 6-Cl2-CH₃-4-(CF₂)₅CF₃ 186 i-C₃H₇ H 0 6-Cl 3-Cl-4-OCHF₂ 187 i-C₃H₇ H 0 6-Cl2-Cl-4-OCF₃ 188 i-C₃H₇ H 0 6-Cl 2-Br-4-OCF₃ 189 i-C₃H₇ H 0 6-Cl2-Br-4-CF(CF₃)₂ 190 i-C₃H₇ H 0 6-I 2-CH₃-3-Cl 191 i-C₃H₇ H 0 6-I2-CH₃-4-Cl 192 i-C₃H₇ H 0 6-I 2-CH₃-5-Cl 193 i-C₃H₇ H 0 6-I 2-CH₃-4-Br194 i-C₃H₇ H 0 6-I 2-CH₃-4-I 195 i-C₃H₇ H 0 6-I 2-CH₃-4-OCH₃ 196 i-C₃H₇H 0 6-I 2,3-(CH₃)₂-4-OCH₃ 197 i-C₃H₇ H 0 6-I 2-Cl-4-CF₃ 198 i-C₃H₇ H 06-I 2-Cl-4-CF(CF₃)₂ 199 i-C₃H₇ H 0 6-I 2-CH₃-4-CF₃ 200 i-C₃H₇ H 0 6-I2-CH₃-4-CF₂CF₃ 201 i-C₃H₇ H 0 6-I 2-CH₃-4-OCF₂CCl₃ 202 i-C₃H₇ H 0 6-I2-CH₃-4-CF₂CF₂CF₃ 203 i-C₃H₇ H 0 6-I 2-CH₃-4-CF(CF₃)₂ 204 i-C₃H₇ H 0 6-I2-CH₃-4-(CF₂)₃CF₃ 205 i-C₃H₇ H 0 6-I 2-CH₃-4-(CF₂)₅CF₃ 206 i-C₃H₇ H 06-I 3-Cl-4-OCHF₂ 207 i-C₃H₇ H 0 6-I 2-Cl-4-OCF₃ 208 i-C₃H₇ H 0 6-I2-Br-4-OCF₃ 209 i-C₃H₇ H 0 6-I 2-Br-4-CF(CF₃)₂ 210 i-C₃H₇ H 0 6-I2-CH₃-4-CF₃ 211 i-C₃H₇ H 0 4-I 2-CH₃-4-CF₂CF₃ 212 i-C₃H₇ H 0 4-I2-CH₃-4-OCF₂CCl₃ 213 i-C₃H₇ H 0 4-I 2-CH₃-4-CF₂CF₂CF₃ 214 i-C₃H₇ H 0 4-I2-CH₃-4-CF(CF₃)₂ 215 i-C₃H₇ H 0 4-I 2-CH₃-4-(CF₂)₃CF₃ 216 i-C₃H₇ H 0 4-I2-CH₃-4-(CF₂)₅CF₃ 217 i-C₃H₇ H 0 4-I 3-Cl-4-OCHF₂ 218 i-C₃H₇ H 0 4-I2-Cl-4-OCF₃ 219 i-C₃H₇ H 0 4-I 2-Br-4-OCF₃

 

TABLE 2 (Z¹ = Z² = O, R³ = H, Het = Q2, B¹ = B² = B³ = B⁴ = C) Physicalproperty No R¹ R² p Xn Ym m.p. ° C. 220 i-C₃H₇ H 0 H 2-CH₃-4-CF₃ 221i-C₃H₇ H 0 H 2-CH₃-4-OCHF₂ 222 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂ 223 i-C₃H₇ H 0H 2-CH₃-4-OCBrF₂ 224 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CHF₂ 225 i-C₃H₇ H 0 H2-CH₃-3-OCF₂CHClF 226 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CCl₂F 227 i-C₃H₇ H 0 H2-CH₃-4-OCF₂CBrF₂ 228 i-C₃H₇ H 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 229 i-C₃H₇ H 0 H2-CH₃-4-CF₂CF₃ 230 i-C₃H₇ H 0 H 2-CH₃-4-CF(CF₃)₂ 234-236 231 i-C₃H₇ H 0H 2-CH₃-4-SCF₂CBrF₂ 232 i-C₃H₇ H 0 H 2-CH₃-4-SCH₂CF₂CHF₂ 233 i-C₃H₇ H 0H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 234 i-C₃H₇ H 0 H 2-Cl-4-CF₃ 235 i-C₃H₇ H 0 H2-Cl-4-CF(CF₂)₂ 236 i-C₃H₇ H 0 H 3-Cl-4-OCHF₂ 237 i-C₃H₇ H 0 H3-F-4-OCHF₂ 238 i-C₃H₇ H 0 H 2-Cl-4-OCF₃ 239 i-C₃H₇ H 1 H 2-CH₃-4-CF₂CF₃240 i-C₃H₇ H 1 H 2-CH₃-4-CF(CF₃)₂ 241 i-C₃H₇ H 0 2-Cl 2-CH₃-4-CF₂CF₃ 242i-C₃H₇ H 0 2-Cl 2-CH₃-4-CF(CF₃)₂ 315 (dec.) 243 i-C₃H₇ H 0 2-Cl2-CH₃-4-OCF₂CBrFCF₃ 244 i-C₃H₇ H 0 2-Cl 2-CH₃-4-OCF₂CHFOCF₃ 245 i-C₃H₇ H0 2-CI 2-CH₃-4-OCHF₂-5-Cl 246 i-C₃H₇ H 0 2-Cl 2-CH₃-4-OCF₂CHF₂-5-Cl 247i-C₃H₇ H 0 2-Cl 2-CH₃-4-SCHF₂ 248 i-C₃H₇ H 0 2-Cl 2-CH₃-4-(F₅—PhO) 249i-C₃H₇ H 0 2-Cl 2-CH₃-4-(5-CF₃-2-Pyr—O) 250 i-C₃H₇ H 0 2-Cl2-CH₃-4-(3-Cl-5-CF₂-2-Pyr—O) 251 i-C₃H₇ H 0 2-Cl 2-CH₃-4-P═O(OC₂H₅)₂ 252i-C₃H₇ H 0 2-Cl 2-CH₃-4-OP═S(OCH₃)₂ 253 i-C₃H₇ H 0 2-Cl 2-CF₃-4-OCHF₂254 i-C₃H₇ H 0 2-Cl 3-CF₃-4-OCHF₂ 255 i-C₃H₇ H 0 2-Cl 3-N═C(CF₃)-O-4 256i-C₃H₇ H 0 2-Cl 3-N═C(CF₃)-NH-4 257 i-C₃H₇ H 0 2-Cl 3-N═C(CF₃)-N(CH₃)-4258 i-C₃H₇ H 0 2-Cl 2-CH₃-4-OCF3 229-231 259 i-C₃H₇ H 0 2-Br 2-CH₃-4-CF₃260 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCHF₂ 261 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₃ 262i-C₃H₇ H 0 2-Br 2-CH₃-4-OCBrF₂ 263 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₂CHF₂ 264i-C₃H₇ H 0 2-Br 2-CH₃-3-OCF₂CHClF 265 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₂CCl₂F266 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₂CBrF₂ 267 i-C₃H₇ H 0 2-Br2-CH₃-4-OCH₂CF₂CHF₂ 268 i-C₃H₇ H 0 2-Br 2-CH₃-4-CF₂CF₃ 269 i-C₃H₇ H 02-Br 2-CH₃-4-CF(CF₃)₂ 270 i-C₃H₇ H 0 2-Br 2-CH₃-4-SCF₂CBrF₂ 271 i-C₃H₇ H0 2-Br 2-CH₃-4-SCH₂CF₂CHF₂ 272 i-C₃H₇ H 0 2-Br 2-CH₃-4-SO₂CH₂CF₂CHF₂ 273i-C₃H₇ H 0 2-Br 2-Cl-4-CF₃ 274 i-C₃H₇ H 0 2-Br 2-Cl-4-CF(CF₂)₂ 275i-C₃H₇ H 0 2-Br 3-Cl-4-OCHF₂ 276 i-C₃H₇ H 0 2-Br 3-F-4-OCHF₂ 277 i-C₃H₇H 0 2-Br 2-Cl-4-OCF₃ 278 i-C₃H₇ H 0 2-Br 2-Br-4-OCF₃ 279 i-C₃H₇ H 0 2-Br3,5-Cl₂-4-OCHF₂ 280 i-C₃H₇ H 0 2-I 2-CH₃-4-CF(CF₃)₂ 281 i-C₃H₇ H 0 2-I2-CH₃-4-(CF₂)₃CF₃ 282 i-C₃H₇ H 0 2-I 2-CH₃-4-OCH₃ 283 i-C₃H₇ H 0 2-I2-CH₃-4-OCH₂CF₂CHF₂ 284 i-C₃H₇ H 0 2-I 2,4-(CH₃)₂-3-OCHF₂ 285 i-C₃H₇ H 02-I 2,3-(CH₃)₂-4-OCH₃ 286 i-C₃H₇ H 0 2-I 2-Cl-4-OCF₃ 287 i-C₃H₇ H 0 2-I2-Br-4-OCF₃ 288 i-C₃H₇ H 0 2-I 2-CH₃-4-OCHF₂ 289 i-C₃H₇ H 0 2-I2-CH₃-4-OCF₃ 290 i-C₃H₇ H 0 2-I 2-CH₃-4-OCBrF₂ 291 i-C₃H₇ H 0 2-I2-CH₃-4-OCF₂CHFCF₃ 292 i-C₃H₇ H 0 2-I 2-CH₃-4-OCF₂CHClF 293 i-C₃H₇ H 02-I 2-CH₃-4-OCF₂CHF₂ 294 i-C₃H₇ H 0 2-I 2-CH₃-3-Cl-4-OCHF₂ 295 i-C₃H₇ H0 2-I 2,3-(CH₃)₂-4-OCHF₂ 296 i-C₃H₇ H 0 2-I 2-CH₃-4-SCH₃ 297 i-C₃H₇ H 02-I 2-CH₃-4-(3-CF₃—PhO) 298 i-C₃H₇ H 0 2-I 2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O)299 i-C₃H₇ H 0 5-Cl 2-CH₃-4-(5-CF₃-2-Pyr—O) 300 i-C₃H₇ H 0 5-Cl-3-OCH₂O-4- 301 i-C₃H₇ H 0 5-Cl 4-CF₃ 302 i-C₃H₇ H 0 5-Cl 4-OCF₃ 303i-C₃H₇ H 0 5-Cl 2,3-(CH₃)₂ 304 i-C₃H₇ H 0 5-Cl 2,4,6-(CH₃)₃ 305 i-C₃H₇ H0 5-Cl 2-CH₃-3-Cl 306 i-C₃H₇ H 0 5-Cl 2-CH₃-4-Cl 307 i-C₃H₇ H 0 5-Cl2-CH₃-5-Cl 308 i-C₃H₇ H 0 5-Cl 2,3-(CH₃)₂-4-Cl 309 i-C₃H₇ H 0 5-Cl2,4-(CH₃)₂-3-Cl 310 i-C₃H₇ H 0 5-Cl 2-C₂H₅-4-Cl 311 i-C₃H₇ H 0 5-Cl2-CH₃-4-Br 312 i-C₃H₇ H 0 5-Cl 2,3-(CH₃)₂-4-Br 313 i-C₃H₇ H 0 5-Cl2-CH₃-4-I 314 i-C₃H₇ H 0 5-Cl 2-CH₃-4-F 315 i-C₃H₇ H 0 5-Cl 2-Cl-4-CF₃316 i-C₃H₇ H 0 5-Cl 2-CH₃-4-CF₃ 317 i-C₃H₇ H 0 5-Cl 2-CH₃-4-CF(CF₃)₂ 318i-C₃H₇ H 0 5-Cl 2-CH₃-4-(CF₂)₃CF₃ 319 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCH₂CF₂CHF₂ 320 i-C₃H₇ H 0 5-Cl 2,4-(CH₃)₂-3-OCHF₂ 321 i-C₃H₇ H0 5-Cl 2,3-(CH₃)₂-4-OCH₃ 322 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCH₃ 323 i-C₃H₇ H 05-Cl 2-Cl-4-OCF₃ 324 i-C₃H₇ H 0 5-Cl 2-Br-4-OCF₃ 325 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCHF₂ 326 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCF₃ 327 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCBrF₂ 328 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCF₂CHFCF₃ 329 i-C₃H₇ H 05-Cl 2-CH₃-4-OCF₂CHClF 330 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCF₂CHF₂ 331 i-C₃H₇ H0 5-Cl 2,3-(CH₃)₂-4-OCHF₂ 332 i-C₃H₇ H 0 5-Cl 2-CH₃-3-Cl-4-OCHF₂ 333i-C₃H₇ H 0 5-Cl 2-CH₃-4-SCH₃ 334 i-C₃H₇ H 0 5-Cl 2-CH₃-4-(3-CF₃—PhO) 335i-C₃H₇ H 0 5-Cl 2-CH₃-4-(5-CF₃-2-Pyr—O) 336 i-C₃H₇ H 0 5-Cl2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O) 337 i-C₃H₇ H 0 5-Cl -3-OCH₂O-4- 338 i-C₃H₇H 0 5-Cl 2-Cl-4-OCHF₂ 339 i-C₃H₇ H 0 5-I 4-Cl 340 i-C₃H₇ H 0 5-I 4-Br341 i-C₃H₇ H 0 5-I 4-I 342 i-C₃H₇ H 0 5-I 3-CF₃ 343 i-C₃H₇ H 0 5-I 4-CF₃344 i-C₃H₇ H 0 5-I 4-CF₂CF₂CF₃ 345 i-C₃H₇ H 0 5-I 4-CF(CF₃)₂ 346 i-C₃H₇H 0 5-I 4-OCF₃ 347 i-C₃H₇ H 0 5-I 4-OCF₂CHFOCF₃ 348 i-C₃H₇ H 0 5-I4-SCHF₂ 349 i-C₃H₇ H 0 5-I 4-SCH₂CF₃ 350 i-C₃H₇ H 0 5-I 4-SCF₂CHF₂ 351i-C₃H₇ H 0 5-I 4-SCF₂CBrF₂ 352 i-C₃H₇ H 0 5-I 4-SCF(CF₃)₂ 353 i-C₃H₇ H 05-I 4-S(CF₂)₃CF₃ 354 i-C₃H₇ H 0 5-I 3,4-F₂ 355 i-C₃H₇ H 0 5-I 2-CH₃-3-Cl356 i-C₃H₇ H 0 5-I 2-CH₃-4-Cl 357 i-C₃H₇ H 0 5-I 2-CH₃-5-Cl 358 i-C₃H₇ H0 5-I 2,4-(CH₃)₂-3-Cl 359 i-C₃H₇ H 0 5-I 2,3-(CH₃)₂-4-Cl 360 i-C₃H₇ H 05-I 2-Cl-4-CF₃ 361 i-C₃H₇ H 0 5-I 2-Cl-4-CF₂CF₃ 362 i-C₃H₇ H 0 5-I2-Cl-4-CF₂CF₂CF₃ 363 i-C₃H₇ H 0 5-I 2-Cl-4-CF(CF₃)₂ 364 i-C₃H₇ H 0 5-I2-Cl-4-(CF₂)₃CF₃ 365 i-C₃H₇ H 0 5-I 2-C₂H₅-4-CF(CF₃)₂ 366 i-C₃H₇ H 0 5-I2-CH₃-4-Br 367 i-C₃H₇ H 0 5-I 2-CH₃-4-I 368 i-C₃H₇ H 0 5-I 2-CH₃-4-F 369i-C₃H₇ H 0 5-I 2-Cl-4-CF₃ 370 i-C₃H₇ H 0 5-I 2-CH₃-3-CF₃ 371 i-C₃H₇ H 05-I 2-CH₃-4-CF₃ 372 i-C₃H₇ H 0 5-I 2-CH₃-4-CF₂CF₃ 373 i-C₃H₇ H 0 5-I2-CH₃-4-CF₂CF₂CF₃ 374 i-C₃H₇ H 0 5-I 2-CH₃-4-CF(CF₃)₂ 375 i-C₃H₇ H 0 5-I2-CH₃-4-(CF₂)₃CF₃ 376 i-C₃H₇ H 0 5-I 2-CH₃-4-OCH₃ 377 i-C₃H₇ H 0 5-I2-CH₃-4-O—C₃H₇-i 378 i-C₃H₇ H 0 5-I 2,3-(CH₃)₂-4-OCH₃ 379 i-C₃H₇ H 0 5-I2-CH₃-4-OCH₂CF₃ 380 i-C₃H₇ H 0 5-I 2-CH₃-4-OCF₂CBrF₂ 381 i-C₃H₇ H 0 5-Br2-CH₃-4-OCF₂CCl₂F 382 i-C₃H₇ H 0 5-Br 3-F-4-OCHF₂ 383 i-C₃H₇ H 0 5-Br3,5-Cl₂-4-OCHF₂ 384 i-C₃H₇ H 0 5-Br 3-OCH₃-4-OCHF₂ 385 i-C₃H₇ H 0 5-Br3,4-(OCHF₂)₂ 386 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₃ 387 i-C₃H₇ H 0 5-Br2-CH₃-4-OCHF₂ 388 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCH₂CF₂CHF₂ 389 i-C₃H₇ H 05-Br 2-CH₃-4-OCBrF₂ 390 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHF₂ 391 i-C₃H₇ H 05-Br 2-CH₃-4-OCF₂CHF₂-5-Cl 392 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHClF 393i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHFCF₃ 394 i-C₃H₇ H 0 5-Br2-CH₃-4-OCF₂CBrFCF₃ 395 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHFOCF₃ 396 i-C₃H₇ H0 5-Br 2-CH₃-4-OCHF₂-5-Cl 397 i-C₃H₇ H 0 5-Br 2-CH₃-4-(F₅—PhO) 398i-C₃H₇ H 0 5-Br 2-CH₃-4-(3-CF₃—PhO) 399 i-C₃H₇ H 0 5-Br2-CH₃-4-(5-CF₃-2-Pyr—O) 400 i-C₃H₇ H 0 2-CH₃ 2-CH₃-4-OCF₃ 401 i-C₃H₇ H 02-CH₃ 2-CH₃-4-CF₂CF₃ 402 i-C₃H₇ H 0 2-CH₃ 2-CH₃-4-CF₂CF₂CF₃ 403 i-C₃H₇ H0 2-CH₃ 2-CH₃-4-CF(CF₃)₂ 404 i-C₃H₇ H 0 2-CH₃ 2-CH₃-4-(CF₂)₃CF₃ 405i-C₃H₇ H 0 2-CH₃ 2-Cl-4-CF(CF₃)₂ 406 i-C₃H₇ H 0 2-CH₃ 2-Cl-4-(CF₂)₃CF₃407 i-C₃H₇ H 0 2-CH₃ 2-C₂H₅-4-CF(CF₃)₂ 408 i-C₃H₇ H 0 2-CH₃ 2-F-4-CF₂CF₃409 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-OCF₃ 410 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-CF₂CF₃411 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-CF₂CF₂CF₃ 412 i-C₃H₇ H 0 2-CF₃2-CH₃-4-CF(CF₃)₂ 413 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-(CF₂)₃CF₃ 414 i-C₃H₇ H 02-CF₃ 2-Cl-4-CF(CF₃)₂ 415 i-C₃H₇ H 0 2-CF₃ 2-Cl-4-(CF₂)₃CF₃ 416 i-C₃H₇ H0 2-CF₃ 2-C₂H₅-4-CF(CF₃)₂ 417 i-C₃H₇ H 0 2-CF₃ 2-F-4-CF₂CF₃ 418 i-C₃H₇ H0 2-CF₃ 2-C₂H₅-4-CF₂CF₃ 419 i-C₃H₇ H 0 2-CF₃ 2-Br-4-CF₂CF₃ 420 i-C₃H₇ H0 5-CH₃ 2-CH₃-4-OCF₃ 421 i-C₃H₇ H 0 5-CH₃ 2-CH₃-4-CF₂CF₃ 422 i-C₃H₇ H 05-CH₃ 2-CH₃-4-CF₂CF₂CF₃ 423 i-C₃H₇ H 0 5-CH₃ 2-CH₃-4-CF(CF₃)₂ 424 i-C₃H₇H 0 5-CH₃ 2-CH₃-4-(CF₂)₃CF₃ 425 i-C₃H₇ H 0 5-CH₃ 2-Cl-4-CF(CF₃)₂ 426i-C₃H₇ H 0 5-CH₃ 2-Cl-4-(CF₂)₃CF₃ 427 i-C₃H₇ H 0 5-CH₃ 2-C₂H₅-4-CF(CF₃)₂428 i-C₃H₇ H 0 5-CH₃ 2-F-4-CF₂CF₃ 429 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-OCF₃ 430i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF₃CF₃ 431 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF₂CF₂CF₃432 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF(CF₃)₂ 433 i-C₃H₇ H 0 5-CF₃2-CH₃-4-(CF₂)₃CF₃ 434 i-C₃H₇ H 0 5-CF₃ 2-Cl-4-CF(CF₃)₂ 435 i-C₃H₇ H 05-CF₃ 2-Cl-4-(CF₂)₃CF₃ 436 i-C₃H₇ H 0 5-CF₃ 2-C₂H₅-4-CF₂CF₃ 437 i-C₃H₇ H0 5-CF₃ 2-C₂H₅-4-CF(CF₃)₂ 438 i-C₃H₇ H 0 5-CF₃ 2-F-4-CF₂CF₃ 439 i-C₃H₇ H0 5-CF₃ 2-Br-4-CF₂CF₃ 440 i-C₃H₇ H 0 5-CF₃ 2-Br-4-CF(CF₃)₂

 

TABLE 3 (R¹ = CH(CH₃)CH₂SCH₃, R³ = H, Z¹ = Z² = O, Het = Q2, B¹ = B² =B³ = B⁴ = C) Physical property No R² p Xn Ym m.p. ° C. 441 H 0 H2-CH₃-4-OCF₃ 442 H 0 H 2-CH₃-4-CF₂CF₃ 443 H 0 H 2-CH₃-4-CF₂CF₂CF₃ 444 H0 H 2-CH₃-4-CF(CF₃)₂ 445 H 0 H 2-CH₃-4-(CF₂)₃CF₃ 446 H 0 H2-Cl-4-CF(CF₃)₂ 447 H 0 H 2-Cl-4-(CF₂)₃CF₃ 448 H 0 H 2-C₂H₅-4-CF₂CF₃ 449H 0 H 2-C₂H₅-4-CF(CF₃)₂ 450 H 0 H 2-F-4-CF₂CF₃ 451 H 0 H 2-Br-4-CF₂CF₃452 H 0 H 2-Br-4-CF(CF₃)₂ 453 H 0 2-Cl 2-CH₃-4-CF₂CF₃ 454 H 0 2-Cl2-CH₃-4-CF(CF₃)₂ 455 H 0 5-Cl 2-CH₃-4-CF(CF₃)₂ 456 H 0 2-I2-CH₃-4-CF(CF₃)₂ 457 H 0 2-I 2-CH₃-4-CF₂CF₃ 458 H 0 2-I 2-Cl-4-CF(CF₃)₂459 H 0 5-I 2-CH₃-4-CF(CF₃)₂ 460 H 0 5-I 2-CH₃-4-CF₂CF₃

 

TABLE 4 (R¹ = C(CH₃)₂CH₂SCH₃, R³ = H, Z¹ = Z² = O, Het = Q2, B¹ = B² =B³ = B⁴ = C) Physical property No R² p Xn Ym m.p. ° C. 461 H 0 H2-CH₃-4-OCF₃ 462 H 0 H 2-CH₃-4-CF₂CF₃ 463 H 0 H 2-CH₃-4-CF₂CF₂CF₃ 464 H0 H 2-CH₃-4-CF(CF₃)₂ 148-149 465 H 0 H 2-CH₃-4-(CF₂)₃CF₃ 466 H 0 H2-Cl-4-CF(CF₃)₂ 467 H 0 H 2-Cl-4-(CF₂)₃CF₃ 468 H 0 H 2-C₂H₅-4-CF₂CF₃ 469H 0 H 2-C₂H₅-4-CF(CF₃)₂ 470 H 0 H 2-F-4-CF₂CF₃ 471 H 0 H 2-Br-4-CF₂CF₃472 H 0 H 2-Br-4-CF(CF₃)₂ 473 H 0 2-Cl 2-CH₃-4-CF₂CF₃ 474 H 0 2-Cl2-CH₃-4-CF(CF₃)₂ 475 H 0 5-I 2-CH₃-4-CF(CF₃)₂ 476 H 0 2-I2-CH₃-4-CF(CF₃)₂ 477 H 0 2-I 2-CH₃-4-CF₂CF₃ 478 H 0 2-I 2-Cl-4-CF(CF₃)₂479 H 0 5-I 2-CH₃-4-CF(CF₃)₂ 480 H 0 5-I 2-CH₃-4-CF₂CF₃

 

TABLE 5 (R² = R³ = H, Z¹ = Z² = O, Het = Q2, p = 0, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ Xn Ym m.p. ° C. 481 CH(CH₃)CH₂SC₂H₅ H2-CH₃-4-OCF₃ 482 CH(CH₃)CH₂SC₂H₅ H 2-CH₃-4-CF₂CF₃ 483 CH(CH₃)CH₂SC₂H₅ H2-CH₃-4-CF₂CF₂CF₃ 484 C(CH₃)₂CH₂SOCH₃ H 2-CH₃-4-CF(CF₃)₂ 180-182 485CH(CH₃)CH₂SC₂H₅ 2-Cl 2-CH₃-4-(CF₂)₃CF₃ 486 CH(CH₃)CH₂SC₂H₅ 2-I2-Cl-4-CF(CF₃)₂ 487 C(CH₃)₂CH₂SC₂H₅ H 2-CH₃-4-OCF₃ 488 C(CH₃)₂CH₂SC₂H₅ H2-CH₃-4-CF₂CF₃ 489 C(CH₃)₂CH₂SC₂H₅ H 2-CH₃-4-CF₂CF₂CF₃ 490C(CH₃)₂CH₂SC₂H₅ 5-Cl 2-CH₃-4-CF(CF₃)₂ 491 C(CH₃)₂CH₂SC₂H₅ 5-Br2-CH₃-4-(CF₂)₃CF₃ 492 C(CH₃)₂CH₂SC₂H₅ 5-I 2-Cl-4-CF(CF₃)₂ 493CH(CH₃)CH₂NHAc 2-Cl 2-CH₃-4-OCF₃ 494 CH(CH₃)CH₂NHAc 5-Cl 2-CH₃-4-CF₂CF₃495 CH(CH₃)CH₂NHAc 5-I 2-CH₃-4-CF₂CF₂CF₃ 496 CH(CH₃)CH₂NHAc 2-I2-CH₃-4-CF(CF₃)₂ 497 C(CH₃)₂CH₂NHAc 2-Cl 2-CH₃-4-(CF₂)₃CF₃ 498C(CH₃)₂CH₂NHAc 5-I 2-Cl-4-CF(CF₃)₂ 499 CH(CH₃)C₂H₄OCH₃ 2-Cl2-CH₃-4-CF(CF₃)₂ 500 CH(CH₃)C₂H₄OCH₃ 2-I 2-CH₃-4-CF(CH₃)₂ 501C(CH₃)₂C₂H₄OCH₃ 5-I 2-CH₃-4-CF(CF₃)₂

 

TABLE 6 (Z¹ = Z² = O, R³ = H, Het = Q3, B¹ = B² = B³ = B⁴ = C) Physicalproperty No R¹ R² p Xn Ym m.p. ° C. 502 i-C₃H₇ H 0 H 2-CH₃-4-CF₃ 503i-C₃H₇ H 0 H 2-CH₃-4-OCHF₂ 504 i-C₃H₇ H 0 H 2-CH₃-4-OCF₃ 505 i-C₃H₇ H 0H 2-CH₃-4-OCBrF₂ 506 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CHF₂ 507 i-C₃H₇ H 0 H2-CH₃-3-OCF₂CHClF 508 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CCl₂F 509 i-C₃H₇ H 0 H2-CH₃-4-OCF₂CBrF₂ 510 i-C₃H₇ H 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 511 i-C₃H₇ H 0 H2-CH₃-4-CF₂CF₃ 512 i-C₃H₇ H 0 H 2-CH₃-4-CF(CF₃)₂ 206-208 513 i-C₃H₇ H 0H 2-CH₃-4-SCF₂CBrF₂ 514 i-C₃H₇ H 0 H 2-CH₃-4-SCH₂CF₂CHF₂ 515 i-C₃H₇ H 0H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 516 i-C₃H₇ H 0 H 2-Cl-4-CF₃ 517 i-C₃H₇ H 0 H2-Cl-4-CF(CF₂)₂ 518 i-C₃H₇ H 0 H 3-Cl-4-OCHF₂ 519 i-C₃H₇ H 0 H3-F-4-OCHF₂ 520 i-C₃H₇ H 0 H 2-Cl-4-OCF₃ 521 i-C₃H₇ H 1 H 2-CH₃-4-CF₂CF₃522 i-C₃H₇ H 1 H 2-CH₃-4-CF(CF₃)₂ 523 i-C₃H₇ H 0 2-Cl 2-CH₃-4-CF₂CF₃ 524i-C₃H₇ H 0 2-Cl 2-CH₃-4-CF(CF₃)₂ 275-277 525 i-C₃H₇ H 0 2-Cl2-CH₃-4-OCF₂CBrFCF₃ 526 i-C₃H₇ H 0 2-Cl 2-CH₃-4-OCF₂CHFOCF₃ 527 i-C₃H₇ H0 2-Cl 2-CH₃-4-OCHF₂-5-Cl 528 i-C₃H₇ H 0 2-Cl 2-CH₃-4-OCF₂CHF₂-5-Cl 529i-C₃H₇ H 0 2-Cl 2-CH₃-4-SCHF₂ 530 i-C₃H₇ H 0 2-Cl 2-CH₃-4-(F₅—PhO) 531i-C₃H₇ H 0 2-Cl 2-CH₃-4-(5-CF₃-2-Pyr—O) 532 i-C₃H₇ H 0 2-Cl2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O) 533 i-C₃H₇ H 0 2-Cl 2-CH₃-4-P═O(OC₂H₅)₂ 534i-C₃H₇ H 0 2-Cl 2-CH₃-4-OP═S(OCH₃)₂ 535 i-C₃H₇ H 0 2-Cl 2-CF₃-4-OCHF₂536 i-C₃H₇ H 0 2-Cl 3-CF₃-4-OCHF₂ 537 i-C₃H₇ H 0 2-Cl 3-N═C(CF₃)—O-4 538i-C₃H₇ H 0 2-Cl 3-N═C(CF₃)—NH-4 540 i-C₃H₇ H 0 2-Cl 3-N═C(CF₃)—N(CH₃)-4541 i-C₃H₇ H 0 2-Cl 2-CH₃-4-OCHF₂ 542 i-C₃H₇ H 0 2-Br 2-CH₃-4-CF₃ 543i-C₃H₇ H 0 2-Br 2-CH₃-4-OCHF₂ 544 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₃ 545i-C₃H₇ H 0 2-Br 2-CH₃-4-OCBrF₂ 546 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₂CHF₂ 547i-C₃H₇ H 0 2-Br 2-CH₃-3-OCF₂CHClF 548 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₂CCl₂F549 i-C₃H₇ H 0 2-Br 2-CH₃-4-OCF₂CBrF₂ 550 i-C₃H₇ H 0 2-Br2-CH₃-4-OCH₂CF₂CHF₂ 551 i-C₃H₇ H 0 2-Br 2-CH₃-4-CF₂CF₃ 552 i-C₃H₇ H 02-Br 2-CH₃-4-CF(CF₃)₂ 553 i-C₃H₇ H 0 2-Br 2-CH₃-4-SCF₂CBrF₂ 554 i-C₃H₇ H0 2-Br 2-CH₃-4-SCH₂CF₂CHF₂ 555 i-C₃H₇ H 0 2-Br 2-CH₃-4-SO₂CH₂CF₂CHF₂ 556i-C₃H₇ H 0 2-Br 2-Cl-4-CF₃ 557 i-C₃H₇ H 0 2-Br 2-Cl-4-CF(CF₂)₂ 558i-C₃H₇ H 0 2-Br 3-Cl-4-OCHF₂ 559 i-C₃H₇ H 0 2-Br 3-F-4-OCHF₂ 560 i-C₃H₇H 0 2-Br 2-Cl-4-OCF₃ 561 i-C₃H₇ H 0 2-Br 2-Br-4-OCF₃ 562 i-C₃H₇ H 0 2-Br3,5-Cl₂-4-OCHF₂ 563 i-C₃H₇ H 0 2-I 2-CH₃-4-CF(CF₃)₂ 564 i-C₃H₇ H 0 2-I2-CH₃-4-(CF₂)₃CF₃ 565 i-C₃H₇ H 0 2-I 2-CH₃-4-OCH₃ 566 i-C₃H₇ H 0 2-I2-CH₃-4-OCH₂CF₂CHF₂ 567 i-C₃H₇ H 0 2-I 2,4-(CH₃)₂-3-OCHF₂ 568 i-C₃H₇ H 02-I 2,3-(CH₃)₂-4-OCH₃ 569 i-C₃H₇ H 0 2-I 2-Cl-4-OCF₃ 570 i-C₃H₇ H 0 2-I2-Br-4-OCF₃ 571 i-C₃H₇ H 0 2-I 2-CH₃-4-OCHF₂ 572 i-C₃H₇ H 0 2-I2-CH₃-4-OCF₃ 573 i-C₃H₇ H 0 2-I 2-CH₃-4-OCBrF₂ 574 i-C₃H₇ H 0 2-I2-CH₃-4-OCF₂CHFCF₃ 575 i-C₃H₇ R 0 2-I 2-CH₃-4-OCF₂CHClF 576 i-C₃H₇ H 02-I 2-CH₃-4-OCF₂CHF₂ 577 i-C₃H₇ H 0 2-I 2-CH₃-3-Cl-4-OCHF₂ 578 i-C₃H₇ H0 2-I 2,3-(CH₃)₂-4-OCHF₂ 579 i-C₃H₇ H 0 2-I 2-CH₃-4-SCH₃ 580 i-C₃H₇ H 02-I 2-CH₃-4-(3-CF₃—PhO) 581 i-C₃H₇ H 0 2-I 2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O)582 i-C₃H₇ H 0 5-Cl 2-CH₃-4-(5-CF₃-2-Pyr—O) 583 i-C₃H₇ H 0 5-Cl-3-OCH₂O-4- 584 i-C₃H₇ H 0 5-Cl 4-CF₃ 585 i-C₃H₇ H 0 5-Cl 4-OCF₃ 586i-C₃H₇ H 0 5-Cl 2,3-(CH₃)₂ 587 i-C₃H₇ H 0 5-Cl 2,4,6-(CH₃)₃ 588 i-C₃H₇ H0 5-Cl 2-CH₃-3-Cl 589 i-C₃H₇ H 0 5-Cl 2-CH₃-4-Cl 590 i-C₃H₇ H 0 5-Cl2-CH₃-5-Cl 591 i-C₃H₇ H 0 5-Cl 2,3-(CH₃)₂-4-Cl 592 i-C₃H₇ H 0 5-Cl2,4-(CH₃)₂-3-Cl 593 i-C₃H₇ H 0 5-Cl 2-C₂H₅-4-Cl 594 i-C₃H₇ H 0 5-Cl2-CH₃-4-Br 595 i-C₃H₇ H 0 5-Cl 2,3-(CH₃)₂-4-Br 596 i-C₃H₇ H 0 5-Cl2-CH₃-4-I 597 i-C₃H₇ H 0 5-Cl 2-CH₃-4-F 598 i-C₃H₇ H 0 5-Cl 2-Cl-4-CF₃599 i-C₃H₇ H 0 5-Cl 2-CH₃-4-CF₃ 600 i-C₃H₇ H 0 5-Cl 2-CH₃-4-CF(CF₃)₂ 601i-C₃H₇ H 0 5-Cl 2-CH₃-4-(CF₂)₃CF₃ 602 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCH₂CF₂CHF₂ 603 i-C₃H₇ H 0 5-Cl 2,4-(CH₃)₂-3-OCHF₂ 604 i-C₃H₇ H0 5-Cl 2,3-(CH₃)₂-4-OCH₃ 605 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCH₃ 606 i-C₃H₇ H 05-Cl 2-Cl-4-OCF₃ 607 i-C₃H₇ H 0 5-Cl 2-Br-4-OCF₃ 608 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCHF₂ 609 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCF₃ 610 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCBrF₂ 611 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCF₂CHFCF₃ 612 i-C₃H₇ H 05-Cl 2-CH₃-4-OCF₂CHClF 613 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCF₂CHF₂ 614 i-C₃H₇ H0 5-Cl 2,3-(CH₃)₂-4-OCHF₂ 615 i-C₃H₇ H 0 5-Cl 2-CH₃-3-Cl-4-OCHF₂ 616i-C₃H₇ H 0 5-Cl 2-CH₃-4-SCH₃ 617 i-C₃H₇ H 0 5-Cl 2-CH₃-4-(3-CF₃—PhO) 618i-C₃H₇ H 0 5-Cl 2-CH₃-4-(5-CF₃-2-Pyr—O) 619 i-C₃H₇ H 0 5-Cl2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O) 620 i-C₃H₇ H 0 5-Cl -3-OCH₂O-4- 621 i-C₃H₇H 0 5-Cl 2-Cl-4-OCHF₂ 622 i-C₃H₇ H 0 5-I 4-Cl 623 i-C₃H₇ H 0 5-I 4-Br624 i-C₃H₇ H 0 5-I 4-I 625 i-C₃H₇ H 0 5-I 3-CF₃ 626 i-C₃H₇ H 0 5-I 4-CF₃627 i-C₃H₇ H 0 5-I 4-CF₂CF₂CF₃ 628 i-C₃H₇ H 0 5-I 4-CF(CF₃)₂ 629 i-C₃H₇H 0 5-I 4-OCF₃ 630 i-C₃H₇ H 0 5-I 4-OCF₂CHFOCF₃ 631 i-C₃H₇ H 0 5-I4-SCHF₂ 632 i-C₃H₇ H 0 5-I 4-SCH₂CF₃ 633 i-C₃H₇ H 0 5-I 4-SCF₂CHF₂ 634i-C₃H₇ H 0 5-I 4-SCF₂CBrF₂ 635 i-C₃H₇ H 0 5-I 4-SCF(CF₃)₂ 636 i-C₃H₇ H 05-I 4-S(CF₂)₃CF₃ 637 i-C₃H₇ H 0 5-I 3,4-F₂ 638 i-C₃H₇ H 0 5-I 2-CH₃-3-Cl639 i-C₃H₇ H 0 5-I 2-CH₃-4-Cl 640 i-C₃H₇ H 0 5-I 2-CH₃-5-Cl 641 i-C₃H₇ H0 5-I 2,4-(CH₃)₂-3-Cl 642 i-C₃H₇ H 0 5-I 2,3-(CH₃)₂-4-Cl 643 i-C₃H₇ H 05-I 2-Cl-4-CF₃ 644 i-C₃H₇ H 0 5-I 2-Cl-4-CF₂CF₃ 645 i-C₃H₇ H 0 5-I2-Cl-4-CF₂CF₂CF₃ 646 i-C₃H₇ H 0 5-I 2-Cl-4-CF(CF₃)₂ 647 i-C₃H₇ H 0 5-I2-Cl-4-(CF₂)₃CF₃ 648 i-C₃H₇ H 0 5-I 2-C₂H₅-4-CF(CF₃)₂ 649 i-C₃H₇ H 0 5-I2-CH₃-4-Br 650 i-C₃H₇ H 0 5-I 2-CH₃-4-I 651 i-C₃H₇ H 0 5-I 2-CH₃-4-F 652i-C₃H₇ H 0 5-I 2-Cl-4-CF₃ 653 i-C₃H₇ H 0 5-I 2-CH₃-3-CF₃ 654 i-C₃H₇ H 05-I 2-CH₃-4-CF₃ 655 i-C₃H₇ H 0 5-I 2-CH₃-4-CF₂CF₃ 656 i-C₃H₇ H 0 5-I2-CH₃-4-CF₂CF₂CF₃ 657 i-C₃H₇ H 0 5-I 2-CH₃-4-CF(CF₃)₂ 658 i-C₃H₇ H 0 5-I2-CH₃-4-(CF₂)₃CF₃ 659 i-C₃H₇ H 0 5-I 2-CH₃-4-OCH₃ 660 i-C₃H₇ H 0 5-I2-CH₃-4-O—C₃H₇-i 661 i-C₃H₇ H 0 5-I 2,3-(CH₃)₂-4-OCH₃ 662 i-C₃H₇ H 0 5-I2-CH₃-4-OCH₂CF₃ 663 i-C₃H₇ H 0 5-I 2-CH₃-4-OCF₂CBrF₂ 664 i-C₃H₇ H 0 5-Br2-CH₃-4-OCF₂CCl₂F 665 i-C₃H₇ H 0 5-Br 3-F-4-OCHF₂ 666 i-C₃H₇ H 0 5-Br3,5-Cl₂-4-OCHF₂ 667 i-C₃H₇ H 0 5-Br 3-OCH₃-4-OCHF₂ 668 i-C₃H₇ H 0 5-Br3,4-(OCHF₂)₂ 669 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₃ 670 i-C₃H₇ H 0 5-Br2-CH₃-4-OCHF₂ 671 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCH₂CF₂CHF₂ 672 i-C₃H₇ H 05-Br 2-CH₃-4-OCBrF₂ 673 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHF₂ 674 i-C₃H₇ H 05-Br 2-CH₃-4-OCF₂CHF₂-5-Cl 675 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHClF 676i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHFCF₃ 677 i-C₃H₇ H 0 5-Br2-CH₃-4-OCF₂CBrFCF₃ 678 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₂CHFOCF₃ 679 i-C₃H₇ H0 5-Br 2-CH₃-4-OCHF₂-5-Cl 680 i-C₃H₇ H 0 5-Br 2-CH₃-4-(F₅—PhO) 681i-C₃H₇ H 0 5-Br 2-CH₃-4-(3-CF₃—PhO) 682 i-C₃H₇ H 0 5-Br2-CH₃-4-(5-CF₃-2-Pyr—O) 683 i-C₃H₇ H 0 2-CH₃ 2-CH₃-4-OCF₃ 684 i-C₃H₇ H 02-CH₃ 2-CH₃-4-CF₂CF₃ 685 i-C₃H₇ H 0 2-CH₃ 2-CH₃-4-CF₂CF₂CF₃ 686 i-C₃H₇ H0 2-CH₃ 2-CH₃-4-CF(CF₃)₂ 687 i-C₃H₇ H 0 2-CH₃ 2-CH₃-4-(CF₂)₃CF₃ 688i-C₃H₇ H 0 2-CH₃ 2-Cl-4-CF(CF₃)₂ 689 i-C₃H₇ H 0 2-CH₃ 2-Cl-4-(CF₂)₃CF₃690 i-C₃H₇ H 0 2-CH₃ 2-C₂H₅-4-CF(CF₃)₂ 691 i-C₃H₇ H 0 2-CH₃ 2-F-4-CF₂CF₃692 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-OCF₃ 693 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-CF₂CF₃694 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-CF₂CF₂CF₃ 695 i-C₃H₇ H 0 2-CF₃2-CH₃-4-CF(CF₃)₂ 696 i-C₃H₇ H 0 2-CF₃ 2-CH₃-4-(CF₂)₃CF₃ 697 i-C₃H₇ H 02-CF₃ 2-Cl-4-CF(CF₃)₂ 698 i-C₃H₇ H 0 2-CF₃ 2-Cl-4-(CF₂)₃CF₃ 699 i-C₃H₇ H0 2-CF₃ 2-C₂H₅-4-CF(CF₃)₂ 700 i-C₃H₇ H 0 2-CF₃ 2-F-4-CF₂CF₃ 701 i-C₃H₇ H0 2-CF₃ 2-C₂H₅-4-CF₂CF₃ 702 i-C₃H₇ H 0 2-CF₃ 2-Br-4-CF₂CF₃ 703 i-C₃H₇ H0 5-CH₃ 2-CH₃-4-OCF₃ 704 i-C₃H₇ H 0 5-CH₃ 2-CH₃-4-CF₂CF₃ 705 i-C₃H₇ H 05-CH₃ 2-CH₃-4-CF₂CF₂CF₃ 706 i-C₃H₇ H 0 5-CH₃ 2-CH₃-4-CF(CF₃)₂ 707 i-C₃H₇H 0 5-CH₃ 2-CH₃-4-(CF₂)₃CF₃ 708 i-C₃H₇ H 0 5-CH₃ 2-Cl-4-CF(CF₃)₂ 709i-C₃H₇ H 0 5-CH₃ 2-Cl-4-(CF₂)₃CF₃ 710 i-C₃H₇ H 0 5-CH₃ 2-C₂H₅-4-CF(CF₃)₂711 i-C₃H₇ H 0 5-CH₃ 2-F-4-CF₂CF₃ 712 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-OCF₃ 713i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF₂CF₃ 714 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF₂CF₂CF₃715 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF(CF₃)₂ 716 i-C₃H₇ H 0 5-CF₃2-CH₃-4-(CF₂)₃CF₃ 717 i-C₃H₇ H 0 5-CF₃ 2-Cl-4-CF(CF₃)₂ 718 i-C₃H₇ H 05-CF₃ 2-Cl-4-(CF₂)₃CF₃ 719 i-C₃H₇ H 0 5-CF₃ 2-C₂H₅-4-CF₂CF₃ 720 i-C₃H₇ H0 5-CF₃ 2-C₂H₅-4-CF(CF₃)₂ 721 i-C₃H₇ H 0 5-CF₃ 2-F-4-CF₂CF₃ 722 i-C₃H₇ H0 5-CF₃ 2-Br-4-CF₂CF₃ 723 i-C₃H₇ H 0 5-CF₃ 2-Br-4-CF(CF₃)₂

 

TABLE 7 (R¹ = CH(CH₃)CH₂SCH₃, R³ = H, Z¹ = Z² = O, Het = Q3, B¹ = B² =B³ = B⁴ = C) Physical property No R² p Xn Ym m.p. ° C. 724 H 0 H2-CH₃-4-OCF₃ 725 H 0 H 2-CH₃-4-CF₂CF₃ 726 H 0 H 2-CH₃-4-CF₂CF₂CF₃ 727 H0 H 2-CH₃-4-CF(CF₃)₂ 728 H 0 H 2-CH₃-4-(CF₂)₃CF₃ 729 H 0 H2-Cl-4-CF(CF₃)₂ 730 H 0 H 2-Cl-4-(CF₂)₃CF₃ 731 H 0 H 2-C₂H₅-4-CF₂CF₃ 732H 0 H 2-C₂H₅-4-CF(CF₃)₂ 733 H 0 H 2-F-4-CF₂CF₃ 734 H 0 H 2-Br-4-CF₂CF₃735 H 0 H 2-Br-4-CF(CF₃)₂ 736 H 0 2-Cl 2-CH₃-4-CF₂CF₃ 737 H 0 2-Cl2-CH₃-4-CF(CF₃)₂ 237-239 738 H 0 5-Cl 2-CH₃-4-CF(CF₃)₂ 739 H 0 2-I2-CH₃-4-CF(CF₃)₂ 740 H 0 2-I 2-CH₃-4-CF₂CF₃ 741 H 0 2-I 2-Cl-4-CF(CF₃)₂742 H 0 5-I 2-CH₃-4-CF(CF₃)₂ 743 H 0 5-I 2-CH₃-4-CF₂CF₃

 

TABLE 8 (R¹ = C(CH₃)₂CH₂SCH₃, R³ = H, Z¹ = Z² = O, Het = Q3, B¹ = B² =B³ = B⁴ = C) Physical property No R² p Xn Ym m.p. ° C. 744 H 0 H2-CH₃-4-OCF₃ 745 H 0 H 2-CH₃-4-CF₂CF₃ 746 H 0 H 2-CH₃-4-CF₂CF₂CF₃ 747 H0 H 2-CH₃-4-CF(CF₃)₂ 748 H 0 H 2-CH₃-4-(CF₂)₃CF₃ 749 H 0 H2-Cl-4-CF(CF₃)₂ 750 H 0 H 2-Cl-4-(CF₂)₃CF₃ 751 H 0 H 2-C₂H₅-4-CF₂CF₃ 752H 0 H 2-C₂H₅-4-CF(CF₃)₂ 753 H 0 H 2-F-4-CF₂CF₃ 754 H 0 H 2-Br-4-CF₂CF₃755 H 0 H 2-Br-4-CF(CF₃)₂ 756 H 0 2-Cl 2-CH₃-4-CF₂CF₃ 757 H 0 2-Cl2-CH₃-4-CF(CF₃)₂ 758 H 0 5-I 2-CH₃-4-CF(CF₃)₂ 759 H 0 2-I2-CH₃-4-CF(CF₃)₂ 760 H 0 2-I 2-CH₃-4-CF₂CF₃ 761 H 0 2-I 2-Cl-4-CF(CF₃)₂762 H 0 5-I 2-CH₃-4-CF(CF₃)₂ 763 H 0 5-I 2-CH₃-4-CF₂CF₃

 

TABLE 9 (R² = R³ = H, Z¹ = Z² = O, Het = Q3, p = 0, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ Xn Ym m.p. ° C. 764 CH(CH₃)CH₂SC₂H₅ H2-CH₃-4-OCF₃ 765 CH(CH₃)CH₂SC₂H₅ H 2-CH₃-4-CF₂CF₃ 766 CH(CH₃)CH₂SC₂H₅ H2-CH₃-4-CF₂CF₂CF₃ 767 CH(CH₃)CH₂SC₂H₅ H 2-CH₃-4-CF(CF₃)₂ 768CH(CH₃)CH₂SC₂H₅ 2-Cl 2-CH₃-4-(CF₂)₃CF₃ 769 CH(CH₃)CH₂SC₂H₅ 2-I2-Cl-4-CF(CF₃)₂ 770 C(CH₃)₂CH₂SC₂H₅ H 2-CH₃-4-OCF₃ 771 C(CH₃)₂CH₂SC₂H₅ H2-CH₃-4-CF₂CF₃ 772 C(CH₃)₂CH₂SC₂H₅ H 2-CH₃-4-CF₂CF₂CF₃ 773C(CH₃)₂CH₂SC₂H₅ 5-Cl 2-CH₃-4-CF(CF₃)₂ 774 C(CH₃)₂CH₂SC₂H₅ 5-Br2-CH₃-4-(CF₂)₃CF₃ 775 C(CH₃)₂CH₂SC₂H₅ 5-I 2-Cl-4-CF(CF₃)₂ 776CH(CH₃)CH₂NHAc 2-Cl 2-CH₃-4-OCF₃ 777 CH(CH₃)CH₂NHAc 5-Cl 2-CH₃-4-CF₂CF₃778 CH(CH₃)CH₂NHAc 5-I 2-CH₃-4-CF₂CF₂CF₃ 779 CH(CH₃)CH₂NHAc 2-I2-CH₃-4-CF(CF₃)₂ 780 C(CH₃)₂CH₂NHAc 2-Cl 2-CH₃-4-(CF₂)₃CF₃ 781C(CH₃)₂CH₂NHAc 5-I 2-Cl-4-CF(CF₃)₂ 782 CH(CH₃)C₂H₄OCH₃ 2-Cl2-CH₃-4-CF(CF₃)₂ 783 CH(CH₃)C₂H₄OCH₃ 2-I 2-CH₃-4-CF(CH₃)₂ 784C(CH₃)₂C₂H₄OCH₃ 5-I 2-CH₃-4-CF(CF₃)₂

 

TABLE 10 (Z¹ = Z² = O, R³ = H, Het = Q4, B¹ = B² = B³ = B⁴ = C) Physicalproperty No R¹ R² p Xn Ym m.p. ° C. 785 i-C₃H₇ H 0 H 2-CH₃-4-CF₃ 184-185786 i-C₃H₇ H 0 H 2-CH₃-4-OCHF₂ 787 i-C₃H₇ H 0 H 2-CH₃-4-OCF₃ 788 i-C₃H₇H 0 H 2-CH₃-4-OCBrF₂ 789 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CHF₂ 790 i-C₃H₇ H 0 H2-CH₃-3-OCF₂CHClF 791 i-C₃H₇ H 0 H 2-CH₃-4-OCF₂CCl₂F 792 i-C₃H₇ H 0 H2-CH₃-4-OCF₂CBrF₂ 793 i-C₃H₇ H 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 794 i-C₃H₇ H 0 H2-CH₃-4-CF₂CF₃ paste 795 i-C₃H₇ H 0 H 2-CH₃-4-CF(CF₃)₂ 159-161 796i-C₃H₇ H 0 H 2-CH₃-4-SCF₂CBrF₂ 797 i-C₃H₇ H 0 H 2-CH₃-4-SCH₂CF₂CHF₂ 798i-C₃H₇ H 0 H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 799 i-C₃H₇ H 0 H 2-Cl-4-CF₃ 800i-C₃H₇ H 0 H 2-Cl-4-CF(CF₂)₂ 801 i-C₃H₇ H 0 H 3-Cl-4-OCHF₂ 802 i-C₃H₇ H0 H 3-F-4-OCHF₂ 803 i-C₃H₇ H 1 H 2-CH₃-4-CF₂CF₃ 804 i-C₃H₇ H 1 H2-CH₃-4-CF(CF₃)₂ 108-110 805 C₂H₅ C₂H₅ 0 H 2-CH₃-4-CF₂CF₃ 130-132 806n-C₃H₇ H 0 4-Cl 2-CH₃-4-CF₂CF₃ 807 c-C₃H₅ H 0 4-Cl 2-CH₃-4-CF(CF₃)₂ 808n-C₃H₇ H 0 4-Cl 2-CH₃-4-OCF₂CBrFCF₃ 809 i-C₄H₉ H 0 4-Cl2-CH₃-4-OCF₂CHFOCF₃ 810 i-C₄H₉ H 0 4-Cl 2-CH₃-4-OCHF₂-5-Cl 811 n-C₄H₉ H0 4-Cl 2-CH₃-4-OCF₂CHF₂-5-Cl 812 i-C₃H₇ H 0 4-Cl 2-CH₃-4-SCHF₂ 813i-C₃H₇ H 0 4-Cl 2-CH₃-4-(F₅—PhO) 814 i-C₃H₇ H 0 4-Cl2-CH₃-4-(5-CF₃-2-Pyr—O) 815 i-C₃H₇ H 0 4-Cl 2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O)816 i-C₃H₇ H 0 4-Cl 2-CH₃-4-P═O(OC₂H₅)₂ 817 i-C₃H₇ H 0 4-Cl2-CH₃-4-OP═S(OCH₃)₂ 818 i-C₃H₇ H 0 4-Cl 2-CF₃-4-OCHF₂ 819 i-C₃H₇ H 04-Cl 3-CF₃-4-OCHF₂ 820 i-C₃H₇ H 0 4-Cl 3-N═C(CF₃)—O-4 821 i-C₃H₇ H 04-Cl 2-CH₃-4-CF₂CF₃ 149-152 822 i-C₃H₇ H 0 4-Cl 2-CH₃-4-CF(CF₃)₂ 823c-C₃H₅ H 0 4-Cl 2-CH₃-4-OCHF₂ 824 i-C₃H₇ H 0 4-Cl 2-CH₃-4-CF₃ 825 i-C₃H₇H 0 4-Cl 2-CH₃-4-OCHF₂ 826 i-C₃H₇ H 0 4-Cl 2-CH₃-4-OCF₃ 827 i-C₃H₇ H 04-Cl 2-CH₃-4-OCBrF₂ 828 i-C₃H₇ H 0 4-Cl 2-CH₃-4-OCF₂CHF₂ 829 i-C₃H₇ H 04-Cl 2-CH₃-3-OCF₂CHClF 830 i-C₃H₇ H 0 4-Cl 2-CH₃-4-OCF₂CCl₂F 831 i-C₃H₇H 0 4-Cl 2-CH₃-4-OCF₂CBrF₂ 832 i-C₃H₇ H 0 4-Br 2-CH₃-4-OCH₂CF₂CHF₂ 833i-C₃H₇ H 0 4-Br 2-CH₃-4-CF₂CF₃ 834 i-C₃H₇ H 0 4-Br 2-CH₃-4-CF(CF₃)₂ 835i-C₃H₇ H 0 4-Br 2-CH₃-4-SCF₂CBrF₂ 836 i-C₃H₇ H 0 4-Br2-CH₃-4-SCH₂CF₂CHF₂ 837 i-C₃H₇ H 0 4-Br 2-CH₃-4-SO₂CH₂CF₂CHF₂ 838 i-C₃H₇H 0 4-Br 2-Cl-4-CF₃ 839 i-C₃H₇ H 0 4-Br 2-Cl-4-CF(CF₂)₂ 840 i-C₃H₇ H 04-Br 3-Cl-4-OCHF₂ 841 i-C₃H₇ H 0 4-Br 3-F-4-OCHF₂ 842 i-C₃H₇ H 0 4-Br2-Cl-4-OCF₃ 843 i-C₃H₇ H 0 4-Br 2-Br-4-OCF₃ 844 i-C₃H₇ H 0 4-Br3,5-Cl₂-4-OCHF₂ 845 i-C₃H₇ H 0 4-I 2-CH₃-4-CF(CF₃)₂ 846 i-C₃H₇ H 0 4-I2-CH₃-4-(CF₂)₃CF₃ 847 i-C₃H₇ H 0 4-I 2-CH₃-4-OCH₃ 848 i-C₃H₇ H 0 4-I2-CH₃-4-OCH₂CF₂CHF₂ 849 i-C₃H₇ H 0 4-I 2,4-(CH₃)₂-3-OCHF₂ 850 i-C₃H₇ H 04-I 2,3-(CH₃)₂-4-OCH₃ 851 i-C₃H₇ H 0 4-I 2-Cl-4-OCF₃ 852 i-C₃H₇ H 0 4-I2-Br-4-OCF₃ 853 i-C₃H₇ H 0 4-I 2-CH₃-4-OCHF₂ 854 i-C₃H₇ H 0 4-I2-CH₃-4-OCF₃ 855 i-C₃H₇ H 0 4-I 2-CH₃-4-OCBrF₂ 856 i-C₃H₇ H 0 4-I2-CH₃-4-OCF₂CHFCF₃ 857 i-C₃H₇ H 0 4-I 2-CH₃-4-OCF₂CHClF 858 i-C₃H₇ H 04-I 2-CH₃-4-OCF₂CHF₂ 859 i-C₃H₇ H 0 4-I 2-CH₃-3-Cl-4-OCHF₂ 860 i-C₃H₇ H0 4-I 2,3-(CH₃)₂-4-OCHF₂ 861 i-C₃H₇ H 0 4-I 2-CH₃-4-SCH₃ 862 i-C₃H₇ H 04-I 2-CH₃-4-(3-CF₃—PhO) 863 i-C₃H₇ H 0 4-I 2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O)864 i-C₃H₇ H 0 5-Cl 2-Cl-4-CF₃ 865 i-C₃H₇ H 0 5-Cl 2-CH₃-4-CF₃ 866i-C₃H₇ H 0 5-Cl 2-CH₃-4-CF(CF₃)₂ 867 i-C₃H₇ H 0 5-Cl 2-CH₃-4-(CF₂)₃CF₃868 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCH₂CF₂CHF₂ 869 i-C₃H₇ H 0 5-Cl2,4-(CH₃)₂-3-OCHF₂ 870 i-C₃H₇ H 0 5-Cl 2,3-(CH₃)₂-4-OCH₃ 871 i-C₃H₇ H 05-Cl 2-CH₃-4-OCH₃ 872 i-C₃H₇ H 0 5-Cl 2-Cl-4-OCF₃ 873 i-C₃H₇ H 0 5-Cl2-Br-4-OCF₃ 874 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCHF₂ 875 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCF₃ 876 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCBrF₂ 877 i-C₃H₇ H 0 5-Cl2-CH₃-4-OCF₂CHFCF₃ 878 i-C₃H₇ H 0 5-Cl 2-CH₃-4-OCF₂CHClF 879 i-C₃H₇ H 05-Cl 2-CH₃-4-OCF₂CHF₂ 880 i-C₃H₇ H 0 6-Cl 2-CH₃-4-CF(CF₃)₂ 881 i-C₃H₇ H0 6-Cl 2-CH₃-4-(CF₂)₃CF₃ 882 i-C₃H₇ H 1 6-Cl 2-CH₃-4-CF(CF₃)₂ 883 i-C₃H₇H 1 6-Cl 2-CH₃-4-(CF₂)₃CF₃ 884 i-C₃H₇ H 0 6-Cl 2-CH₃-4-OCH₂CF₂CHF₂ 885i-C₃H₇ H 0 4-I 2-CH₃-4-OCH₂CF₂CHF₂ 886 i-C₃H₇ H 0 4-I 2-CH₃-4-CF(CF₃)₂F₂887 i-C₃H₇ H 0 4-I 2-CH₃-4-(CF₂)₃CF₃ 888 i-C₃H₇ H 0 4-I 2-CH₃-4-CF(CF₃)₂889 i-C₃H₇ H 0 4-I 2-CH₃-4-(CF₂)₃CF 890 i-C₃H₇ H 0 4-I 2-Br-4-OCF₃ 891i-C₃H₇ H 0 4-I 2-CH₃-4-OCHF₂ 892 i-C₃H₇ H 0 4-I 2-CH₃-4-OCF₃ 893 i-C₃H₇H 0 4-I 2-CH₃-4-OCBrF₂ 894 i-C₃H₇ H 0 4-I 2-CH₃-4-OCF₂CHFCF₃ 895 i-C₃H₇H 0 4-I 2-CH₃-4-OCF₂CHClF 896 i-C₃H₇ H 0 5-I 2-CH₃-4-CF₂CF₃ 897 i-C₃H₇ H0 5-I 2-CH₃-4-CF₂CF₂CF₃ 898 i-C₃H₇ H 0 5-I 2-CH₃-4-CF(CF₃)₂ 899 i-C₃H₇ H0 5-I 2-CH₃-4-SCH₃ 900 i-C₃H₇ H 0 5-I 2-CH₃-4-(3-CF₃—PhO) 901 i-C₃H₇ H 05-I 2-CH₃-4-(5-CF₃-2-Pyr—O) 902 i-C₃H₇ H 0 5-I2-CH₃-4-(3-Cl-5-CF₃-2-Pyr—O) 903 i-C₃H₇ H 0 6-I 2-CH₃-4-CF(CF₃)₂ 904i-C₃H₇ H 0 6-I 2-Cl-4-CF₂CF₃ 905 i-C₃H₇ H 0 4-Br 2-Cl-4-CF₃ 906 i-C₃H₇ H0 4-Br 2-Cl-4-CF₂CF₃ 907 i-C₃H₇ H 0 4-Br 2-Cl-4-CF₂CF₂CF₃ 908 i-C₃H₇ H 04-Br 2-Cl-4-CF(CF₃)₂ 909 i-C₃H₇ H 0 4-Br 2-Cl-4-(CF₂)₃CF₃ 910 i-C₃H₇ H 04-Br 2-C₂H₅-4-CF(CF₃)₂ 911 i-C₃H₇ H 0 4-Br 2-CH₃-4-Br 912 i-C₃H₇ H 04-Br 2-CH₃-4-I 913 i-C₃H₇ H 0 4-Br 2-CH₃-4-F 914 i-C₃H₇ H 0 4-Br2-Cl-4-CF₃ 916 i-C₃H₇ H 0 4-Br 2-CH₃-4-CF₃ 917 i-C₃H₇ H 0 4-Br2-CH₃-4-CF₂CF₃ 918 i-C₃H₇ H 0 4-Br 2-CH₃-4-CF₂CF₂CF₃ 919 i-C₃H₇ H 0 4-Br2-CH₃-4-CF(CF₃)₂ 920 i-C₃H₇ H 0 4-Br 2-CH₃-4-(CF₂)₃CF₃ 921 i-C₃H₇ H 04-Br 2-CH₃-4-OCH₃ 922 i-C₃H₇ H 0 4-Br 2-CH₃-4-O—C₃H₇-i 923 i-C₃H₇ H 04-Br 2,3-(CH₃)₂-4-OCH₃ 924 i-C₃H₇ H 0 4-Br 2-CH₃-4-OCH₂CF₃ 925 i-C₃H₇ H0 4-Br 2-CH₃-4-OCF₂CBrF₂ 926 i-C₃H₇ H 0 5-Br 2-CH₃-4-OCF₃ 927 i-C₃H₇ H 05-Br 2-CH₃-4-CF₂CF₃ 928 i-C₃H₇ H 0 5-Br 2-CH₃-4-CF₂CF₂CF₃ 929 i-C₃H₇ H 05-Br 2-CH₃-4-CF(CF₃)₂ 930 i-C₃H₇ H 0 5-Br 2-CH₃-4-(CF₂)₃CF₃ 931 i-C₃H₇ H0 5-Br 2-Cl-4-CF(CF₃)₂ 932 i-C₃H₇ H 0 5-Br 2-Cl-4-(CF₂)₃CF₃ 933 i-C₃H₇ H0 5-Br 2-C₂H₅-4-CF(CF₃)₂ 934 i-C₃H₇ H 0 5-Br 2-F-4-CF₂CF₃ 935 i-C₃H₇ H 06-Br 2-CH₃-4-OCF₃ 936 i-C₃H₇ H 0 6-Br 2-CH₃-4-CF₂CF₃ 937 i-C₃H₇ H 0 6-Br2-CH₃-4-CF₂CF₂CF₃ 938 i-C₃H₇ H 0 6-Br 2-CH₃-4-CF(CF₃)₂ 939 i-C₃H₇ H 06-Br 2-CH₃-4-(CF₂)₃CF₃ 940 i-C₃H₇ H 0 6-Br 2-Cl-4-CF(CF₃)₂ 941 i-C₃H₇ H0 6-Br 2-Cl-4-(CF₂)₃CF₃ 942 i-C₃H₇ H 0 6-Br 2-C₂H₅-4-CF(CF₃)₂ 943 i-C₃H₇H 0 6-Br 2-F-4-CF₂CF₃ 944 i-C₃H₇ H 0 6-Br 2-C₂H₅-4-CF₂CF₃ 945 i-C₃H₇ H 04-CH₃ 2-CH₃-4-OCF₃ 946 i-C₃H₇ H 0 4-CH₃ 2-CH₃-4-CF₂CF₃ 947 i-C₃H₇ H 04-CH₃ 2-CH₃-4-CF₂CF₂CF₃ 948 i-C₃H₇ H 0 4-CH₃ 2-CH₃-4-CF(CF₃)₂ 949 i-C₃H₇H 0 4-CH₃ 2-CH₃-4-(CF₂)₃CF₃ 950 i-C₃H₇ H 0 4-CH₃ 2-Cl-4-CF(CF₃)₂ 951i-C₃H₇ H 0 4-CH₃ 2-Cl-4-(CF₂)₃CF₃ 952 i-C₃H₇ H 0 4-CH₃ 2-C₂H₅-4-CF(CF₃)₂953 i-C₃H₇ H 0 4-CH₃ 2-F-4-CF₂CF₃ 954 i-C₃H₇ H 0 4-CF₃ 2-CH₃-4-OCF₃ 955i-C₃H₇ H 0 4-CF₃ 2-CH₃-4-CF₂CF₃ 956 i-C₃H₇ H 0 4-CF₃ 2-CH₃-4-CF₂CF₂CF₃957 i-C₃H₇ H 0 4-CF₃ 2-CH₃-4-CF(CF₃)₂ 958 i-C₃H₇ H 0 4-CF₃2-CH₃-4-(CF₂)₃CF₃ 959 i-C₃H₇ H 0 4-CF₃ 2-Cl-4-CF(CF₃)₂ 960 i-C₃H₇ H 04-CF₃ 2-Cl-4-(CF₂)₃CF₃ 961 i-C₃H₇ H 0 4-CF₃ 2-C₂H₅-4-CF(CF₃)₂ 962 i-C₃H₇H 0 4-CF₃ 2-F-4-CF₂CF₃ 963 i-C₃H₇ H 0 4-CF₃ 2-C₂H₅-4-CF₂CF₃ 964 i-C₃H₇ H0 4-CF₃ 2-Br-4-CF₂CF₃ 965 i-C₃H₇ H 0 5-CH₃ 2-CH₃-4-OCF₃ 966 i-C₃H₇ H 05-CH₃ 2-CH₃-4-CF₂CF₃ 967 i-C₃H₇ H 0 5-CH₃ 2-CH₃-4-CF₂CF₂CF₃ 968 i-C₃H₇ H0 5-CH₃ 2-CH₃-4-CF(CF₃)₂ 969 i-C₃H₇ H 0 6-CH₃ 2-CH₃-4-(CF₂)₃CF₃ 970i-C₃H₇ H 0 6-CH₃ 2-Cl-4-CF(CF₃)₂ 971 i-C₃H₇ H 0 6-CH₃ 2-Cl-4-(CF₂)₃CF₃972 i-C₃H₇ H 0 6-CH₃ 2-C₂H₅-4-CF(CF₃)₂ 973 i-C₃H₇ H 0 6-CH₃ 2-F-4-CF₂CF₃974 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-OCF₃ 975 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF₂CF₃976 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-CF₂CF₂CF₃ 977 i-C₃H₇ H 0 5-CF₃2-CH₃-4-CF(CF₃)₂ 978 i-C₃H₇ H 0 5-CF₃ 2-CH₃-4-(CF₂)₃CF₃ 979 i-C₃H₇ H 05-CF₃ 2-Cl-4-CF(CF₃)₂ 980 i-C₃H₇ H 0 5-CF₃ 2-Cl-4-(CF₂)₃CF₃ 981 i-C₃H₇ H0 5-CF₃ 2-C₂H₅-4-CF₂CF₃ 982 i-C₃H₇ H 0 5-CF₃ 2-C₂H₅-4-CF(CF₃)₂ 983i-C₃H₇ H 0 6-CF₃ 2-F-4-CF₂CF₃ 984 i-C₃H₇ H 0 6-CF₃ 2-Br-4-CF₂CF₃ 985i-C₃H₇ H 0 6-CF₃ 2-Br-4-CF(CF₃)₂

 

TABLE 11 (R¹ = CH(CH₃)CH₂SCH₃, R³ = H, Z¹ = Z² = O, Het = Q4, B¹ = B² =B³ = B⁴ = C) Physical property No R² p Xn Ym m.p. ° C.  986 H 0 H2-CH₃-4-OCF₃  987 H 0 H 2-CH₃-4-CF₂CF₃  988 H 0 H 2-CH₃-4-CF₂CF₂CF₃  989H 0 H 2-CH₃-4-CF(CF₃)₂ 108-110  990 H 1 H 2-CH₃-4-CF(CF₃)₂ paste  991 H0 H 2-Cl-4-CF(CF₃)₂  992 H 0 H 2-Cl-4-(CF₂)₃CF₃  993 H 0 H2-C₂H₅-4-CF₂CF₃  994 H 0 H 2-C₂H₅-4-CF(CF₃)₂  995 H 0 H 2-F-4-CF₂CF₃ 996 H 0 H 2-Br-4-CF₂CF₃  997 H 0 H 2-Br-4-CF(CF₃)₂  998 H 0 4-Cl2-CH₃-4-CF₂CF₃  999 H 0 4-Cl 2-CH₃-4-CF(CF₃)₂ 237-239 1000 H 0 5-Cl2-CH₃-4-CF(CF₃)₂ 1001 H 0 4-I 2-CH₃-4-CF(CF₃)₂ 1002 H 0 4-I2-CH₃-4-CF₂CF₃ 1003 H 0 4-I 2-Cl-4-CF(CF₃)₂ 1004 H 0 5-I2-CH₃-4-CF(CF₃)₂ 1005 H 0 5-I 2-CH₃-4-CF₂CF₃

 

TABLE 12 (R¹ = C(CH₃)₂CH₂SCH₃, R³ = H, Z¹ = Z² = O, Het = Q4, B¹ = B² =B³ = B⁴ = C) Physical property No R² p Xn Ym m.p. ° C. 1006 H 0 H2-CH₃-4-OCF₃ 1007 H 0 H 2-CH₃-4-CF₂CF₃ 1008 H 0 H 2-CH₃-4-CF₂CF₂CF₃ 1009H 0 H 2-CH₃-4-CF(CF₃)₂ paste 1010 H 0 H 2-CH₃-4-(CF₂)₃CF₃ 1011 H 0 H2-Cl-4-CF(CF₃)₂ 1012 H 0 H 2-Cl-4-(CF₂)₃CF₃ 1013 H 0 H 2-C₂H₅-4-CF₂CF₃1014 H 0 H 2-C₂H₅-4-CF(CF₃)₂ 1015 H 0 H 2-F-4-CF₂CF₃ 1016 H 0 H2-Br-4-CF₂CF₃ 1017 H 0 H 2-Br-4-CF(CF₃)₂ 1018 H 0 4-Cl 2-CH₃-4-CF₂CF₃1019 H 0 4-Cl 2-CH₃-4-CF(CF₃)₂ 1020 H 0 5-Cl 2-CH₃-4-CF(CF₃)₂ 1021 H 04-I 2-CH₃-4-CF(CF₃)₂ 1022 H 0 4-I 2-CH₃-4-CF₂CF₃ 1023 H 0 4-I2-Cl-4-CF(CF₃)₂ 1024 H 0 5-I 2-CH₃-4-CF(CF₃)₂ 1025 H 0 5-I2-CH₃-4-CF₂CF₃

 

TABLE 13 (R² = R³ = H, Z¹ = Z² = O, Het = Q4, p = 0, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ Xn Ym m.p. ° C. 1026 CH(CH₃)CH₂SC₂H₅ H2-CH₃-4-OCF₃ 1027 CH(CH₃)CH₂SC₂H₅ H 2-CH₃-4-CF₂CF₃ 1028 CH(CH₃)CH₂SC₂H₅H 2-CH₃-4-CF₂CF₂CF₃ 1029 CH(CH₃)CH₂SC₂H₅ H 2-CH₃-4-CF(CF₃)₂ 1030CH(CH₃)CH₂SC₂H₅ 4-Cl 2-CH₃-4-(CF₂)₃CF₃ 1031 CH(CH₃)CH₂SC₂H₅ 4-I2-Cl-4-CF(CF₃)₂ 1032 C(CH₃)₂CH₂SC₂H₅ H 2-CH₃-4-OCF₃ 1033 C(CH₃)₂CH₂SC₂H₅H 2-CH₃-4-CF₂CF₃ 1034 C(CH₃)₂CH₂SC₂H₅ H 2-CH₃-4-CF₂CF₂CF₃ 1035C(CH₃)₂CH₂SC₂H₅ 5-Cl 2-CH₃-4-CF(CF₃)₂ 1036 C(CH₃)₂CH₂SC₂H₅ 5-Br2-CH₃-4-(CF₂)₃CF₃ 1037 C(CH₃)₂CH₂SC₂H₅ 5-I 2-Cl-4-CF(CF₃)₂ 1038CH(CH₃)CH₂NHAc 4-Cl 2-CH₃-4-OCF₃ 1039 CH(CH₃)CH₂NHAc 5-Cl 2-CH₃-4-CF₂CF₃1040 CH(CH₃)CH₂NHAc 5-I 2-CH₃-4-CF₂CF₂CF₃ 1041 CH(CH₃)CH₂NHAc 4-I2-CH₃-4-CF(CF₃)₂ 1042 C(CH₃)₂CH₂NHAc 4-Cl 2-CH₃-4-(CF₂)₃CF₃ 1043C(CH₃)₂CH₂NHAc 5-I 2-Cl-4-CF(CF₃)₂ 1044 CH(CH₃)C₂H₄OCH₃ 4-Cl2-CH₃-4-CF(CF₃)₂ 1045 CH(CH₃)C₂H₄OCH₃ 4-I 2-CH₃-4-CF(CH₃)₂ 1046C(CH₃)₂C₂H₄OCH₃ 5-I 2-CH₃-4-CF(CF₃)₂

 

TABLE 14 (Z¹ = Z² = O, Het = Q4, B¹ = B² = B³ = B⁴ = C) Physicalproperty No R¹ R² R³ Xn Ym m.p. ° C. 1047 C₂H₅ C₂H₅ CH₃ H 2-CH₃-4-OCF₃1048 C₂H₅ C₂H₅ CH₃ 4-Cl 2-CH₃-4-CF₂CF₃ paste 1049 C₂H₅ C₂H₅ CH₃ 4-Cl2-CH₃-4-CF₂CF₂CF₃ 1050 C₂H₅ C₂H₅ CH₃ 4-Cl 2-CH₃-4-CF(CF₃)₂ 1051 C₂H₅C₂H₅ CH₃ 4-I 2-CH₃-4-(CF₂)₃CF₃ 1052 C₂H₅ C₂H₅ CH₃ 4-I 2-Cl-4-CF(CF₃)₂1053 C₂H₅ C₂H₅ C₂H₅ 4-I 2-CH₃-4-OCF₃ 1054 C₂H₅ C₂H₅ C₂H₅ 4-Cl2-CH₃-4-CF₂CF₃ 1055 C₂H₅ C₂H₅ C₂H₅ 4-Cl 2-CH₃-4-CF₂CF₂CF₃ 1056 C₂H₅ C₂H₅C₂H₅ 4-I 2-CH₃-4-CF(CF₃)₂ 1057 C₂H₅ C₂H₅ C₂H₅ 4-I 2-CH₃-4-(CF₂)₃CF₃ 1058C₂H₅ C₂H₅ C₂H₅ 4-I 2-Cl-4-CF(CF₃)₂

 

TABLE 15 (Z¹ = Z² = O, R² = R³ = H, q = 0, Het = Q5, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ p Xn Ym m.p. ° C. 1059 i-C₃H₇ 0 H 2-CH₃-4-CF₃1060 i-C₃H₇ 0 H 2-CH₃-4-OCF₃ 1061 i-C₃H₇ 0 H 2-CH₃-4-OCF₂CHF₂ 1062i-C₃H₇ 0 H 2-CH₃-4-CH₂CF₂CHF₂ 1063 i-C₃H₇ 0 H 2-CH₃-4-CF₂CF₃ 1064 i-C₃H₇0 H 2-CH₃-4-CF(CF₃)₂ 1065 i-C₃H₇ 0 H 2-CH₃-4-SCH₂CF₂CHF₂ 1066 i-C₃H₇ 0 H2-CH₃-4-SO₂CH₂CF₂CHF₂ 1067 i-C₃H₇ 0 H 2-Cl-4-CF(CF₂)₂ 1068 i-C₃H₇ 0 H2-Cl-4-CF₂CF₃ 1069 i-C₃H₇ 0 H 2-C₂H₅-4-CF(CF₃)₂ 1070 i-C₃H₇ 0 H2-F-4-CF₂CF₃ 1071 i-C₃H₇ 0 5-Cl 2-CH₃-4-CF₂CF₃ 1072 i-C₃H₇ 0 5-Cl2-CH₃-4-CF(CF₃)₂ 1073 i-C₃H₇ 0 5-I 2-CH₃-4-CF₂CF₃ 1074 i-C₃H₇ 0 5-I2-CH₃-4-CF(CF₃)₂ 1075 i-C₃H₇ 0 5-CH₃ 2-CH₃-4-CF₂CF₃ 1076 i-C₃H₇ 0 5-CH₃2-CH₃-4-CF(CF₃)₂ 1077 i-C₃H₇ 0 5-CF₃ 2-CH₃-4-CF(CF₃)₂ 1078CH(CH₃)CH₂SCH₃ 0 H 2-CH₃-4-CF₂CF₃ 1079 CH(CH₃)CH₂SCH₃ 0 H2-CH₃-4-CF(CF₃)₂ 1080 CH(CH₃)CH₂SC₂H₅ 0 H 2-CH₃-4-CF₂CF₃ 1081CH(CH₃)CH₂SC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1082 C(CH₃)₂CH₂SC₂H₅ 0 H2-CH₃-4-CF₂CF₃ 1083 C(CH₃)₂CH₂SC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1084CH(CH₃)CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1085 CH(CH₃)CH₂NHAc 0 H2-CH₃-4-CF(CF₃)₂ 1086 C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1087C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF(CF₃)₂ 1088 CH(CH₃)C₂H₄OCH₃ 0 H2-CH₃-4-CF₂CF₃ 1089 CH(CH₃)C₂H₄OCH₃ 0 H 2-CH₃-4-CF(CF₃)₂

 

TABLE 16 (Z¹ = Z² = O, R² = R³ = H, q = 0, Het = Q6, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ p Xn Ym m.p. ° C. 1090 i-C₃H₇ 0 H 2-CH₃-4-CF₃1091 i-C₃H₇ 0 H 2-CH₃-4-OCF₃ 1092 i-C₃H₇ 0 H 2-CH₃-4-OCF₂CHF₂ 1093i-C₃H₇ 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 1094 i-C₃H₇ 0 H 2-CH₃-4-CF₂CF₃ 1095i-C₃H₇ 0 H 2-CH₃-4-CF(CF₃)₂ 191-193 1096 i-C₃H₇ 0 H 2-CH₃-4-SCH₂CF₂CHF₂1097 i-C₃H₇ 0 H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1098 i-C₃H₇ 0 H 2-Cl-4-CF(CF₂)₂1099 i-C₃H₇ 0 H 2-Cl-4-CF₂CF₃ 1100 i-C₃H₇ 0 H 2-C₂H₅-4-CF(CF₃)₂ 1101i-C₃H₇ 0 H 2-F-4-CF₂CF₃ 1102 i-C₃H₇ 0 3-Cl 2-CH₃-4-CF₂CF₃ 1103 i-C₃H₇ 06-Cl 2-CH₃-4-CF(CF₃)₂ 1104 i-C₃H₇ 0 3-I 2-CH₃-4-CF₂CF₃ 1105 i-C₃H₇ 0 6-I2-CH₃-4-CF(CF₃)₂ 1106 i-C₃H₇ 0 3-CH₃ 2-CH₃-4-CF₂CF₃ 1107 i-C₃H₇ 0 6-CH₃2-CH₃-4-CF(CF₃)₂ 1108 i-C₃H₇ 0 3-CF₃ 2-CH₃-4-CF(CF₃)₂ 1109CH(CH₃)CH₂SOCH₃ 0 H 2-CH₃-4-CF₂CF₃ 1110 CH(CH₃)CH₂SCH₃ 0 H2-CH₃-4-CF(CF₃)₂ 85-95 1111 CH(CH₃)CH₂SOC₂H₅ 0 H 2-CH₃-4-CF₂CF₃ 1112CH(CH₃)CH₂SC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1113 C(CH₃)₂CH₂SC₂H₅ 0 H2-CH₃-4-CF₂CF₃ 1114 C(CH₃)₂CH₂SOC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1115CH(CH₃)CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1116 CH(CH₃)CH₂NHAc 0 H2-CH₃-4-CF(CF₃)₂ 1117 C(CH₃)₂CH₂NHAC 0 H 2-CH₃-4-CF₂CF₃ 1118C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF(CF₃)₂ 1119 CH(CH₃)C₂H₄OCH₃ 0 H2-CH₃-4-CF₂CF₃ 1120 CH(CH₃)C₂H₄OCH₃ 0 H 2-CH₃-4-CF(CF₃)₂ 1121CH(CH₃)C₂H₄OCH₃ 0 H 2-C₂H₅-4-CF(CF₃)₂

 

TABLE 17 (Z¹ = Z² = O, R² = R³ = H, q = 0, Het = Q7, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ p Xn Ym m.p. ° C. 1122 i-C₃H₇ 0 H 2-CH₃-4-CF₃1123 i-C₃H₇ 0 H 2-CH₃-4-OCF₃ 1124 i-C₃H₇ 0 H 2-CH₃-4-OCF₂CHF₂ 1125i-C₃H₇ 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 1126 i-C₃H₇ 0 H 2-CH₃-4-CF₂CF₃ 1127i-C₃H₇ 0 H 2-CH₃-4-CF(CF₃)₂ 204-206 1128 i-C₃H₇ 0 H 2-CH₃-4-SCH₂CF₂CHF₂1129 i-C₃H₇ 0 H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1130 i-C₃H₇ 0 H 2-Cl-4-CF(CF₂)₂1131 i-C₃H₇ 0 H 2-Cl-4-CF₂CF₃ 1132 i-C₃H₇ 0 H 2-C₂H₅-4-CF(CF₃)₂ 1133i-C₃H₇ 0 H 2-F-4-CF₂CF₃ 1134 i-C₃H₇ 0 5-Cl 2-CH₃-4-CF₂CF₃ 1135 i-C₃H₇ 06-Cl 2-CH₃-4-CF(CF₃)₂ 1136 i-C₃H₇ 0 5-I 2-CH₃-4-CF₂CF₃ 1137 i-C₃H₇ 0 6-I2-CH₃-4-CF(CF₃)₂ 1138 i-C₃H₇ 0 5-CH₃ 2-CH₃-4-CF₂CF₃ 1139 i-C₃H₇ 0 6-CH₃2-CH₃-4-CF(CF₃)₂ 1140 i-C₃H₇ 0 5-CF₃ 2-CH₃-4-CF(CF₃)₂ 1141CH(CH₃)CH₂SOCH₃ 0 H 2-CH₃-4-CF₂CF₃ 1142 CH(CH₃)CH₂SCH₃ 0 H2-CH₃-4-CF(CF₃)₂ 1143 CH(CH₃)CH₂SOC₂H₅ 0 H 2-CH₃-4-CF₂CF₃ 1144CH(CH₃)CH₂SC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1145 C(CH₃)₂CH₂SC₂H₅ 0 H2-CH₃-4-CF₂CF₃ 1146 C(CH₃)₂CH₂SOC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1147CH(CH₃)CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1148 CH(CH₃)CH₂NHAc 0 H2-CH₃-4-CF(CF₃)₂ 1149 C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1150C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF(CF₃)₂ 1151 CH(CH₃)C₂H₄OCH₃ 0 H2-CH₃-4-CF₂CF₃ 1152 CH(CH₃)C₂H₄OCH₃ 0 H 2-CH₃-4-CF(CF₃)₂

 

TABLE 18 (Z¹ = Z² = O, R² = R³ = H, q = O, Het = Q8, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ p Xn Ym m.p. ° C. 1153 i-C₃H₇ 0 H 2-CH₃-4-CF₃1154 i-C₃H₇ 0 H 2-CH₃-4-OCF₃ 1155 i-C₃H₇ 0 H 2-CH₃-4-OCF₂CHF₂ 1156i-C₃H₇ 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 1157 i-C₃H₇ 0 H 2-CH₃-4-CF₂CF₃ 1158i-C₃H₇ 0 H 2-CH₃-4-CF(CF₃)₂ 192-194 1159 i-C₃H₇ 0 H 2-CH₃-4-SCH₂CF₂CHF₂1160 i-C₃H₇ 0 H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1161 i-C₃H₇ 0 H 2-Cl-4-CF(CF₂)₂1162 i-C₃H₇ 0 H 2-Cl-4-CF₂CF₃ 1163 i-C₃H₇ 0 H 2-C₂H₅-4-CF(CF₃)₂ 1164i-C₃H₇ 0 H 2-F-4-CF₂CF₃ 1165 i-C₃H₇ 0 6-Cl 2-CH₃-4-CF₂CF₃ 1166 i-C₃H₇ 06-Cl 2-CH₃-4-CF(CF₃)₂ 1167 i-C₃H₇ 0 6-I 2-CH₃-4-CF₂CF₃ 1168 i-C₃H₇ 0 6-I2-CH₃-4-CF(CF₃)₂ 1169 i-C₃H₇ 0 2-CH₃ 2-CH₃-4-CF₂CF₃ 1170 i-C₃H₇ 0 2-SCH₃2-CH₃-4-CF(CF₃)₂ 204-206 1171 i-C₃H₇ 0 6-CF₃ 2-CH₃-4-CF(CF₃)₂ 1172CH(CH₃)CH₂SOCH₃ 0 H 2-CH₃-4-CF₂CF₃ 1173 CH(CH₃)CH₂SCH₃ 0 2-SCH₃2-CH₃-4-CF(CF₃)₂ 168-170 1174 CH(CH₃)CH₂SOC₂H₅ 0 H 2-CH₃-4-CF₂CF₃ 1175CH(CH₃)CH₂SC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1176 C(CH₃)₂CH₂SC₂H₅ 0 H2-CH₃-4-CF₂CF₃ 1177 C(CH₃)₂CH₂SOC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1178CH(CH₃)CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1179 CH(CH₃)CH₂NHAc 0 H2-CH₃-4-CF(CF₃)₂ 1180 C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1181C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF(CF₃)₂ 1182 CH(CH₃)C₂H₄OCH₃ 0 H2-CH₃-4-CF₂CF₃ 1183 CH(CH₃)C₂H₄OCH₃ 0 H 2-CH₃-4-CF(CF₃)₂

 

TABLE 19 (Z¹ = Z² = O, R² = R³ = H, q = 0, Het = Q9, B¹ = B² = B³ = B⁴ =C) Physical property No R¹ p Xn Ym m.p. ° C. 1184 i-C₃H₇ 0 H 2-CH₃-4-CF₃1185 i-C₃H₇ 0 H 2-CH₃-4-OCF₃ 1186 i-C₃H₇ 0 H 2-CH₃-4-OCF₂CHF₂ 1187i-C₃H₇ 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 1188 i-C₃H₇ 0 H 2-CH₃-4-CF₂CF₃ 1189i-C₃H₇ 0 H 2-CH₃-4-CF(CF₃)₂ 162-164 1190 i-C₃H₇ 0 H 2-CH₃-4-SCH₂CF₂CHF₂1191 i-C₃H₇ 0 H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1192 i-C₃H₇ 0 H 2-Cl-4-CF(CF₂)₂1193 i-C₃H₇ 0 H 2-Cl-4-CF₂CF₃ 1194 i-C₃H₇ 0 H 2-C₂H₅-4-CF(CF₃)₂ 1195i-C₃H₇ 0 H 2-F-4-CF₂CF₃ 1196 i-C₃H₇ 0 6-Cl 2-CH₃-4-CF₂CF₃ 1197 i-C₃H₇ 06-Cl 2-CH₃-4-CF(CF₃)₂ 1198 i-C₃H₇ 0 6-I 2-CH₃-4-CF₂CF₃ 1199 i-C₃H₇ 0 6-I2-CH₃-4-CF(CF₃)₂ 1200 i-C₃H₇ 0 2-CH₃ 2-CH₃-4-CF₂CF₃ 1201 i-C₃H₇ 0 2-SCH₃2-CH₃-4-CF(CF₃)₂ 1202 i-C₃H₇ 0 6-CF₃ 2-CH₃-4-CF(CF₃)₂ 1203CH(CH₃)CH₂SOCH₃ 0 H 2-CH₃-4-CF₂CF₃ 1204 CH(CH₃)CH₂SCH₃ 0 2-SCH₃2-CH₃-4-CF(CF₃)₂ 129-131 1205 CH(CH₃)CH₂SOC₂H₅ 0 H 2-CH₃-4-CF₂CF₃ 1206CH(CH₃)CH₂SC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1207 C(CH₃)₂CH₂SC₂H₅ 0 H2-CH₃-4-CF₂CF₃ 1208 C(CH₃)₂CH₂SOC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1209CH(CH₃)CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1210 CH(CH₃)CH₂NHAc 0 H2-CH₃-4-CF(CF₃)₂ 1211 C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1212C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF(CF₃)₂ 1213 CH(CH₃)C₂H₄OCH₃ 0 H2-CH₃-4-CF₂CF₃ 1214 CH(CH₃)C₂H₄OCH₃ 0 H 2-CH₃-4-CF(CF₃)₂

 

TABLE 20 (Z¹ = Z² = O, R² = R³ = H, q = 0, Het = Q10, B¹ = B² = B³ = B⁴= C) Physical property No R¹ p Xn Ym m.p. ° C. 1215 i-C₃H₇ 0 H2-CH₃-4-CF₃ 1216 i-C₃H₇ 0 H 2-CH₃-4-OCF₃ 1217 i-C₃H₇ 0 H2-CH₃-4-OCF₂CHF₂ 1218 i-C₃H₇ 0 H 2-CH₃-4-OCH₂CF₂CHF₂ 1219 i-C₃H₇ 0 H2-CH₃-4-CF₂CF₃ 1220 i-C₃H₇ 0 H 2-CH₃-4-CF(CF₃)₂ 153-155 1221 i-C₃H₇ 1 H2-CH₃-4-CF(CF₃)₂ paste 1222 i-C₃H₇ 0 H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1223 i-C₃H₇0 H 2-Cl-4-CF(CF₂)₂ 1224 i-C₃H₇ 0 H 2-Cl-4-CF₂CF₃ 1225 i-C₃H₇ 0 H2-C₂H₅-4-CF(CF₃)₂ 1226 i-C₃H₇ 0 H 2-F-4-CF₂CF₃ 1227 i-C₃H₇ 0 6-Cl2-CH₃-4-CF₂CF₃ 1228 i-C₃H₇ 0 6-Cl 2-CH₃-4-CF(CF₃)₂ 1229 i-C₃H₇ 0 6-I2-CH₃-4-CF₂CF₃ 1230 i-C₃H₇ 0 6-I 2-CH₃-4-CF(CF₃)₂ 1231 i-C₃H₇ 0 2-CH₃2-CH₃-4-CF₂CF₃ 1232 i-C₃H₇ 0 2-CH₃ 2-CH₃-4-CF(CF₃)₂ 1233 i-C₃H₇ 0 6-CF₃2-CH₃-4-CF(CF₃)₂ 1234 CH(CH₃)CH₂SCH₃ 0 H 2-CH₃-4-CF₂CF₃ 1235CH(CH₃)CH₂SOCH₃ 0 H 2-CH₃-4-CF₂CF₃ 1236 CH(CH₃)CH₂SCH₃ 0 H2-CH₃-4-CF(CF₃)₂ 1237 CH(CH₃)CH₂SOC₂H₅ 0 R 2-CH₃-4-CF₂CF₃ 1238CH(CH₃)CH₂SC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1239 C(CH₃)₂CH₂SC₂H₅ 0 H2-CH₃-4-CF₂CF₃ 1240 C(CH₃)₂CH₂SOC₂H₅ 0 H 2-CH₃-4-CF(CF₃)₂ 1241CH(CH₃)CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1242 CH(CH₃)CH₂NHAc 0 H2-CH₃-4-CF(CF₃)₂ 1243 C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF₂CF₃ 1244C(CH₃)₂CH₂NHAc 0 H 2-CH₃-4-CF(CF₃)₂ 1245 CH(CH₃)C₂H₄OCH₃ 0 H2-CH₃-4-CF₂CF₃ 1246 CH(CH₃)C₂H₄OCH₃ 0 H 2-CH₃-4-CF(CF₃)₂

 

TABLE 21 (Z¹ = Z² = O, R² = R³ = H, Het = Q11, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1247 i-C₃H₇ O H 2-CH₃-4-CF₂CF₃145-146 1248 i-C₃H₇ O 4,5-(CH₃)₂ 4-OCF₃ 148 1249 t-C₄H₉ O H2-CH₃-4-CF₂CF₃ 139-141 1250 i-C₃H₇ S H 2-CH₃-4-OCH₂CF₂CHF₂ 1251 i-C₃H₇ SH 2-CH₃-4-CF₂CF₃ 164-165 1252 i-C₃H₇ S H 2-CH₃-4-CF(CF₃)₂ 1253 i-C₃H₇ S4-I 2-CH₃-4-CF(CF₃)₂ 1254 i-C₃H₇ S H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1255 i-C₃H₇ S4-I 2-CH₃-4-CF₂CF₃ 202-204 1256 t-C₄H₉ S H 2-CH₃-4-CF₂CF₃ 178-180 1257i-C₃H₇ S H 2-C₂H₅-4-CF(CF₃)₂ 1258 i-C₃H₇ NCH₃ 4-Cl 2-CH₃-4-CF(CF₃)₂ 1259i-C₃H₇ NCH₃ 4-I 2-CH₃-4-CF(CF₃)₂ 1250 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1251i-C₃H₇ NCH₃ H 2-CH₃-4-CF(CF₃)₂ 1252 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1253i-C₃H₇ NPh 4-Cl 2-CH₃-4-CF(CF₃)₂ 1254 i-C₃H₇ NCH₃ 4-CH═CF—CH═CH-52-CH₃-4-CF(CF₃)₂ 189-191 1255 CH(CH₃)CH₂SCH₃ NCH₃ 4-CH═CF—CH═CH-52-CH₃-4-CF(CF₃)₂ 171-173 1256 CH(CH₃)C₂H₄OCH₃ O H 2-CH₃-4-CF(CF₃)₂ 1257CH(CH₃)CH₂SCH₃ S H 2-CH₃-4-CF₂CF₃ 1258 CH(CH₃)CH₂SOCH₃ S H2-CH₃-4-CF₂CF₃ 1259 CH(CH₃)CH₂SOC₂H₅ S H 2-CH₃-4-CF(CF₃)₂ 1260CH(CH₃)CH₂SC₂H₅ S H 2-CH₃-4-CF₂CF₃ 1261 C(CH₃)₂CH₂SC₂H₅ S H2-CH₃-4-CF(CF₃)₂ 1262 C(CH₃)₂CH₂SOC₂H₅ S H 2-CH₃-4-CF₂CF₃ 1263CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1264 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1265 CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF(CF₃)₂

 

TABLE 22 (Z¹ = Z² = O, R³ = H, Het = Q11, B¹ = B² = B³ = B⁴ = C)Physical property No. R¹ R² W Xn Ym m.p. ° C. 1266 C₂H₅ C₂H₅ O H2-CH₃-4-CF₂CF₃ 92-93 1267 C₂H₅ C₂H₅ O H 2-CH₃-4-OCF₃ 81-82 1268 C₂H₅C₂H₅ S H 2-CH₃-4-CF₂CF₃ 160-162 1269 [2-CH₃-4-CF(CF₃)₂]Ph H NCH₃4-CH═CF—CH═CH-5 2-CH₃-4-CF(CF₃)₂ 256-258

TABLE 23 (Z¹ = Z² = O, R² = R³ = H, Het = Q12, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1270 i-C₃H₇ O H 2-CH₃-4-CF₃1271 i-C₃H₇ O H 4-OCF₃ 170 1272 i-C₃H₇ O H 2-CH₃-4-OCF₂CHF₂ 1273 i-C₃H₇S H 2-CH₃-4-OCH₂CF₂CHF₂ 1274 i-C₃H₇ S 2-Cl 2-CH₃-4-CF₂CF₃ 1275 i-C₃H₇ SH 2-CH₃-4-CF(CF₃)₂ 140-145 1276 i-C₃H₇ S 2-I 2-CH₃-4-CF(CF₃)₂ 1277i-C₃H₇ S H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1278 i-C₃H₇ S H 2-Cl-4-CF(CF₂)₂ 1279i-C₃H₇ S H 2-CH₃-5-CF₂CF₃ 125-130 1280 i-C₃H₇ S H 2-CH₃-3-CF₂CF₃ paste1281 i-C₃H₇ S H 2-F-4-CF₂CF₃ 1282 i-C₃H₇ NCH₃ 2-I 2-CH₃-4-CF₂CF₃ 1283i-C₃H₇ NCH₃ 2-I 2-CH₃-4-CF(CF₃)₂ 1284 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1285i-C₃H₇ NCH₃ H 2-CH₃-4-CF(CF₃)₂ 1286 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1287i-C₃H₇ NPh 2-I 2-CH₃-4-CF(CF₃)₂ 1288 i-C₃H₇ NPh H 2-Cl-4-CF₂CF₃ 1289CH(CH₃)CH₂SCH₃ S H 2-CH₃-4-CF₂CF₃ 1290 CH(CH₃)CH₂SOCH₃ S H2-CH₃-4-CF₂CF₃ 1291 CH(CH₃)CH₂SCH₃ S H 2-CH₃-4-CF(CF₃)₂ 1292CH(CH₃)CH₂SOC₂H₅ S H 2-CH₃-4-CF₂CF₃ 1293 CH(CH₃)CH₂SC₂H₅ S H2-CH₃-4-CF(CF₃)₂ 1294 C(CH₃)₂CH₂SC₂H₅ S H 2-CH₃-4-CF₂CF₃ 1295C(CH₃)₂CH₂SOC₂H₅ S H 2-CH₃-4-CF(CF₃)₂ 1296 CH(CH₃)CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1297 CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1298C(CH₃)₂CH₂NHAc S H 2-CH₃-4-CF₂CF₃ 1299 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF(CF₃)₂ 1300 CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF₂CF₃ 1301CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF(CF₃)₂

 

TABLE 24 (Z¹ = Z² = O, R³ = H, Het = Q13, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ R² W Xn Ym m.p. ° C. 1302 i-C₃H₇ H O H2-CH₃-4-CF₃ 1303 i-C₃H₇ H O 4,5-(CH₃)₂ 4-OCF₃ 134 1304 i-C₃H₇ H O H2-CH₃-4-OCF₂CHF₂ 1305 i-C₃H₇ H S H 2-CH₃-4-OCH₂CF₂CHF₂ 1306 i-C₃H₇ H S H2-CH₃-4-OCF₃ 139-141 1307 i-C₃H₇ H S H 2-CH₃-4-CF₂CF₃ 159-161 1308i-C₃H₇ H S 4-I 2-CH₃-4-CF(CF₃)₂ 1309 i-C₃H₇ H S H 2-CH₃-4-CF(CF₃)₂ 1310i-C₃H₇ H S H 2-Cl-4-CF(CF₂)₂ 1311 C₂H₅ C₂H₅ S H 2-CH₃-4-CF₂CF₃ 120-1221312 C₂H₅ C₂H₅ S H 2-C₂H₅-4-CF(CF₃)₂ 1313 C₂H₅ C₂H₅ S H 2-CH₃-4-OCF₃153-155 1314 i-C₃H₇ H NCH₃ 4-I 2-CH₃-4-CF₂CF₃ 1315 i-C₃H₇ H NPh 4-I2-CH₃-4-CF(CF₃)₂ 1316 i-C₃H₇ H NPh H 2-CH₃-4-CF₂CF₃ 1317 i-C₃H₇ H NPh H2-CH₃-4-CF(CF₃)₂ 1318 i-C₃H₇ H NCH₃ H 2-CH₃-4-CF₂CF₃ 1319 i-C₃H₇ H NCH₃4-I 2-CH₃-4-CF(CF₃)₂ 1320 i-C₃H₇ H NCH₃ 4-CH═CF—CH═CH-5 2-CH₃-4-CF(CF₃)₂195-205 1321 CH(CH₃)CH₂SCH₃ H S H 2-CH₃-4-CF₂CF₃ 1322 CH(CH₃)CH₂SOCH₃ HS H 2-CH₃-4-CF₂CF₃ 1323 CH(CH₃)CH₂SCH₃ H S H 2-CH₃-4-CF(CF₃)₂ 1324CH(CH₃)CH₂SOC₂H₅ H S H 2-CH₃-4-CF₂CF₃ 1325 CH(CH₃)CH₂SC₂H₅ H S H2-CH₃-4-CF(CF₃)₂ 1326 C(CH₃)₂CH₂SC₂H₅ H S H 2-CH₃-4-CF₂CF₃ 1327C(CH₃)₂CH₂SOC₂H₅ H S H 2-CH₃-4-CF(CF₃)₂ 1328 CH(CH₃)CH₂NHAc H S H2-CH₃-4-CF₂CF₃ 1329 CH(CH₃)CH₂NHAc H S H 2-CH₃-4-CF(CF₃)₂ 1330C(CH₃)₂CH₂NHAc H S H 2-CH₃-4-CF₂CF₃ 1331 C(CH₃)₂CH₂NHAc H S H2-CH₃-4-CF(CF₃)₂ 1332 CH(CH₃)C₂H₄OCH₃ H S H 2-CH₃-4-CF₂CF₃ 1333CH(CH₃)C₂H₄OCH₃ H S H 2-CH₃-4-CF(CF₃)₂

 

TABLE 25 (Z¹ = Z² = O, R² = R³ = H, Het = Q14, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1334 i-C₃H₇ O H 2-CH₃-4-CF₃1335 i-C₃H₇ O 3-CH₃ 4-OCF₃ 137-138 1336 i-C₃H₇ O H 2-CH₃-4-OCF₂CHF₂ 1337i-C₃H₇ S H 2-CH₃-4-OCH₂CF₂CHF₂ 1338 i-C₃H₇ S 3-Cl 2-CH₃-4-CF₂CF₃ 1339i-C₃H₇ S H 2-CH₃-4-CF(CF₃)₂ 1340 i-C₃H₇ S 3-I 2-CH₃-4-CF(CF₃)₂ 1341i-C₃H₇ S H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1342 i-C₃H₇ S H 2-Cl-4-CF(CF₂)₂ 1343i-C₃H₇ S H 2-Cl-4-CF₂CF₃ 1344 i-C₃H₇ S H 2-C₂H₅-4-CF(CF₃)₂ 1345 i-C₃H₇ SH 2-F-4-CF₂CF₃ 1346 i-C₃H₇ NCH₃ 3-I 2-CH₃-4-CF₂CF₃ 1347 i-C₃H₇ NCH₃ 3-I2-CH₃-4-CF(CF₃)₂ 1348 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1349 i-C₃H₇ NCH₃ H2-CH₃-4-CF(CF₃)₂ 1350 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1351 i-C₃H₇ NPh 3-I2-CH₃-4-CF(CF₃)₂ 1352 i-C₃H₇ NPh H 2-Cl-4-CF₂CF₃ 1352 CH(CH₃)CH₂SCH₃ S H2-CH₃-4-CF₂CF₃ 1353 CH(CH₃)CH₂SOCH₃ S H 2-CH₃-4-CF₂CF₃ 1354CH(CH₃)CH₂SCH₃ S H 2-CH₃-4-CF(CF₃)₂ 1355 CH(CH₃)CH₂SOC₂H₅ S H2-CH₃-4-CF₂CF₃ 1356 CH(CH₃)CH₂SC₂H₅ S H 2-CH₃-4-CF(CF₃)₂ 1357C(CH₃)₂CH₂SC₂H₅ S H 2-CH₃-4-CF₂CF₃ 1358 C(CH₃)₂CH₂SOC₂H₅ S H2-CH₃-4-CF(CF₃)₂ 1359 CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF₂CF₃ 1360CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1361 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1362 C(CH₃)₂CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1363CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF₂CF₃ 1364 CH(CH₃)C₂H₄OCH₃ S H2-CH₃-4-CF(CF₃)₂

 

TABLE 26 (Z¹ = Z² = O, R² = R³ = H, Het = Q15, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1365 i-C₃H₇ O H 2-CH₃-4-CF₃1366 i-C₃H₇ O 5-CH₃ 4-OCF₃ 1367 i-C₃H₇ O H 2-CH₃-4-OCF₂CHF₂ 1368 i-C₃H₇S H 2-CH₃-4-OCH₂CF₂CHF₂ 1369 i-C₃H₇ S 5-Cl 2-CH₃-4-CF₂CF₃ 1370 i-C₃H₇ SH 2-CH₃-4-CF(CF₃)₂ 1371 i-C₃H₇ S 5-I 2-CH₃-4-CF(CF₃)₂ 1372 i-C₃H₇ S H2-CH₃-4-SO₂CH₂CF₂CHF₂ 1373 i-C₃H₇ S H 2-Cl-4-CF(CF₂)₂ 1374 i-C₃H₇ S H2-Cl-4-CF₂CF₃ 1375 i-C₃H₇ S H 2-C₂H₅-4-CF(CF₃)₂ 1376 i-C₃H₇ S H2-F-4-CF₂CF₃ 1377 i-C₃H₇ NCH₃ 5-I 2-CH₃-4-CF₂CF₃ 1378 i-C₃H₇ NCH₃ 5-I2-CH₃-4-CF(CF₃)₂ 1379 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1380 i-C₃H₇ NCH₃ 5-Br2-CH₃-4-CF(CF₃)₂ 134-136 1381 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1382 i-C₃H₇NPh 5-Br 2-CH₃-4-CF(CF₃)₂ 164-166 1383 i-C₃H₇ NPh H 2-Cl-4-CF₂CF₃ 1384CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF₂CF₃ 1385 CH(CH₃)CH₂SOCH₃ O H2-CH₃-4-CF₂CF₃ 1386 CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF(CF₃)₂ 1387CH(CH₃)CH₂SOC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1388 CH(CH₃)CH₂SC₂H₅ O H2-CH₃-4-CF(CF₃)₂ 1389 C(CH₃)₂CH₂SC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1390C(CH₃)₂CH₂SOC₂H₅ S H 2-CH₃-4-CF(CF₃)₂ 1391 CH(CH₃)CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1392 CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1393C(CH₃)₂CH₂NHAc S H 2-CH₃-4-CF₂CF₃ 1394 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF(CF₃)₂ 1395 CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF₂CF₃ 1396CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF(CF₃)₂

 

TABLE 27 (Z¹ = Z² = O, R² = R³ = H, Het = Q16, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1397 i-C₃H₇ O H 2-CH₃-4-CF₃1398 i-C₃H₇ O 5-CH₃ 4-OCF₃ 1399 i-C₃H₇ O H 2-CH₃-4-OCF₂CHF₂ 1400 i-C₃H₇S H 2-CH₃-4-OCH₂CF₂CHF₂ 1401 i-C₃H₇ S 5-Cl 2-CH₃-4-CF₂CF₃ 1402 i-C₃H₇ SH 2-CH₃-4-CF(CF₃)₂ 1403 i-C₃H₇ S 5-I 2-CH₃-4-CF(CF₃)₂ 1404 i-C₃H₇ S H2-CH₃-4-SO₂CH₂CF₂CHF₂ 1405 i-C₃H₇ S H 2-Cl-4-CF(CF₂)₂ 1406 i-C₃H₇ S H2-Cl-4-CF₂CF₃ 1407 i-C₃H₇ S H 2-C₂H₅-4-CF(CF₃)₂ 1408 i-C₃H₇ S H2-F-4-CF₂CF₃ 1409 i-C₃H₇ NCH₃ 5-I 2-CH₃-4-CF₂CF₃ 1410 i-C₃H₇ NCH₃ 5-I2-CH₃-4-CF(CF₃)₂ 1411 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1412 i-C₃H₇ NCH₃ 5-Br2-CH₃-4-CF(CF₃)₂ 165-175 1413 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1414 i-C₃H₇NPh 5-Br 2-CH₃-4-CF(CF₃)₂ 167-169 1415 i-C₃H₇ NPh H 2-Cl-4-CF₂CF₃ 1416CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF₂CF₃ 1417 CH(CH₃)CH₂SOCH₃ O H2-CH₃-4-CF₂CF₃ 1418 CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF(CF₃)₂ 1419CH(CH₃)CH₂SOC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1420 CH(CH₃)CH₂SC₂H₅ O H2-CH₃-4-CF(CF₃)₂ 1421 C(CH₃)₂CH₂SC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1422C(CH₃)₂CH₂SOC₂H₅ S H 2-CH₃-4-CF(CF₃)₂ 1422 CH(CH₃)CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1423 CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1424C(CH₃)₂CH₂NHAc S H 2-CH₃-4-CF₂CF₃ 1425 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF(CF₃)₂ 1426 CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF₂CF₃ 1427CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF(CF₃)₂

 

TABLE 28 (Z¹ = Z² = O, R² = R³ = H, Het = Q17, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1428 i-C₃H₇ O H 2-CH₃-4-CF₃1429 i-C₃H₇ O 3-CH₃ 4-OCF₃ 171-174 1430 i-C₃H₇ O H 2-CH₃-4-OCF₂CHF₂ 1431i-C₃H₇ S H 2-CH₃-4-OCH₂CF₂CHF₂ 1432 i-C₃H₇ S 3-Cl 2-CH₃-4-CF₂CF₃ 1433i-C₃H₇ S H 2-CH₃-4-CF(CF₃)₂ 1434 i-C₃H₇ S 3-I 2-CH₃-4-CF(CF₃)₂ 1435i-C₃H₇ S H 2-CH₃-4-SO₂CH₂CF₂CHF₂ 1436 i-C₃H₇ S H 2-Cl-4-CF(CF₂)₂ 1437i-C₃H₇ S H 2-Cl-4-CF₂CF₃ 1438 i-C₃H₇ S H 2-C₂H₅-4-CF(CF₃)₂ 1439 i-C₃H₇ SH 2-F-4-CF₂CF₃ 1440 i-C₃H₇ NCH₃ 3-I 2-CH₃-4-CF₂CF₃ 1441 i-C₃H₇ NCH₃ 3-I2-CH₃-4-CF(CF₃)₂ 1442 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1443 i-C₃H₇ NCH₃ 3-Br2-CH₃-4-CF(CF₃)₂ 1444 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1445 i-C₃H₇ NPh 3-Br2-CH₃-4-CF(CF₃)₂ 1446 i-C₃H₇ NPh H 2-Cl-4-CF₂CF₃ 1447 CH(CH₃)CH₂SCH₃ O H2-CH₃-4-CF₂CF₃ 1448 CH(CH₃)CH₂SOCH₃ O H 2-CH₃-4-CF₂CF₃ 1449CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF(CF₃)₂ 1450 CH(CH₃)CH₂SOC₂H₅ O H2-CH₃-4-CF₂CF₃ 1451 CH(CH₃)CH₂SC₂H₅ O H 2-CH₃-4-CF(CF₃)₂ 1452C(CH₃)₂CH₂SC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1453 C(CH₃)₂CH₂SOC₂H₅ S H2-CH₃-4-CF(CF₃)₂ 1454 CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF₂CF₃ 1455CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1456 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1457 C(CH₃)₂CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1458CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF₂CF₃ 1459 CH(CH₃)C₂H₄OCH₃ S H2-CH₃-4-CF(CF₃)₂

 

TABLE 29 (Z¹ = Z² = O, R² = R³ = H, Het = Q18, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1460 i-C₃H₇ O H 2-CH₃-4-CF₃1461 i-C₃H₇ O H 4-OCF₃ 1462 i-C₃H₇ O H 2-CH₃-4-OCF₂CHF₂ 1463 i-C₃H₇ S H2-CH₃-4-OCH₂CF₂CHF₂ 1464 i-C₃H₇ S 2-Cl 2-CH₃-4-CF₂CF₃ 1465 i-C₃H₇ S H2-CH₃-4-CF(CF₃)₂ 1466 i-C₃H₇ S 2-I 2-CH₃-4-CF(CF₃)₂ 1467 i-C₃H₇ S H2-CH₃-4-SO₂CH₂CF₂CHF₂ 1468 i-C₃H₇ S H 2-Cl-4-CF(CF₂)₂ 1469 i-C₃H₇ S H2-Cl-4-CF₂CF₃ 1470 i-C₃H₇ S H 2-C₂H₅-4-CF(CF₃)₂ 1471 i-C₃H₇ S H2-F-4-CF₂CF₃ 1472 i-C₃H₇ NCHF₂ 2-I 2-CH₃-4-CF₂CF₃ 1473 i-C₃H₇ NCHF₂ H2-CH₃-4-CF(CF₃)₂ 85-95 1474 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1475 i-C₃H₇NCH₃ 2-Br 2-CH₃-4-CF(CF₃)₂ 1476 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1477 i-C₃H₇NPh 2-Br 2-CH₃-4-CF(CF₃)₂ 1478 i-C₃H₇ NPh H 2-Cl-4-CF₂CF₃ 1479CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF₂CF₃ 1480 CH(CH₃)CH₂SOCH₃ O H2-CH₃-4-CF₂CF₃ 1481 CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF(CF₃)₂ 1482CH(CH₃)CH₂SOC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1483 CH(CH₃)CH₂SC₂H₅ O H2-CH₃-4-CF(CF₃)₂ 1484 C(CH₃)₂CH₂SC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1485C(CH₃)₂CH₂SOC₂H₅ S H 2-CH₃-4-CF(CF₃)₂ 1486 CH(CH₃)CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1487 CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1488C(CH₃)₂CH₂NHAc S H 2-CH₃-4-CF₂CF₃ 1489 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF(CF₃)₂ 1490 CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF₂CF₃ 1491CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF(CF₃)₂

 

TABLE 30 (Z¹ = Z² = O, R² = R³ = H, Het = Q19, B¹ = B² = B³ = B⁴ = C)Physical property No R¹ W Xn Ym m.p. ° C. 1492 i-C₃H₇ O H 2-CH₃-4-CF₃1493 i-C₃H₇ O H 4-OCF₃ 1494 i-C₃H₇ O H 2-CH₃-4-OCF₂CHF₂ 1495 i-C₃H₇ S H2-CH₃-4-OCH₂CF₂CHF₂ 1496 i-C₃H₇ S 2-Cl 2-CH₃-4-CF₂CF₃ 1497 i-C₃H₇ S H2-CH₃-4-CF(CF₃)₂ 1498 i-C₃H₇ S 2-I 2-CH₃-4-CF(CF₃)₂ 1499 i-C₃H₇ S H2-CH₃-4-SO₂CH₂CF₂CHF₂ 1500 i-C₃H₇ S H 2-Cl-4-CF(CF₂)₂ 1501 i-C₃H₇ S H2-Cl-4-CF₂CF₃ 1502 i-C₃H₇ S H 2-C₂H₅-4-CF(CF₃)₂ 1503 i-C₃H₇ S H2-F-4-CF₂CF₃ 1504 i-C₃H₇ NCHF₂ 2-I 2-CH₃-4-CF₂CF₃ 1505 i-C₃H₇ NCHF₂ H2-CH₃-4-CF(CF₃)₂ 70-90 1506 i-C₃H₇ NCH₃ H 2-CH₃-4-CF₂CF₃ 1507 i-C₃H₇NCH₃ 2-Br 2-CH₃-4-CF(CF₃)₂ 1508 i-C₃H₇ NPh H 2-CH₃-4-CF₂CF₃ 1509 i-C₃H₇NPh 2-Br 2-CH₃-4-CF(CF₃)₂ 1510 i-C₃H₇ NPh H 2-Cl-4-CF₂CF₃ 1511CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF₂CF₃ 1512 CH(CH₃)CH₂SOCH₃ O H2-CH₃-4-CF₂CF₃ 1513 CH(CH₃)CH₂SCH₃ O H 2-CH₃-4-CF(CF₃)₂ 1514CH(CH₃)CH₂SOC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1515 CH(CH₃)CH₂SC₂H₅ O H2-CH₃-4-CF(CF₃)₂ 1516 C(CH₃)₂CH₂SC₂H₅ O H 2-CH₃-4-CF₂CF₃ 1517C(CH₃)₂CH₂SOC₂H₅ S H 2-CH₃-4-CF(CF₃)₂ 1518 CH(CH₃)CH₂NHAc S H2-CH₃-4-CF₂CF₃ 1519 CH(CH₃)CH₂NHAc S H 2-CH₃-4-CF(CF₃)₂ 1520C(CH₃)₂CH₂NHAc S H 2-CH₃-4-CF₂CF₃ 1521 C(CH₃)₂CH₂NHAc S H2-CH₃-4-CF(CF₃)₂ 1522 CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF₂CF₃ 1523CH(CH₃)C₂H₄OCH₃ S H 2-CH₃-4-CF(CF₃)₂

 

TABLE 31 (Z¹ = Z² = O, R² = R³ = H, B¹ = B² = B³ = B⁴ = C) Physicalproperty No R¹ W Het Ym m.p. ° C. 1524 i-C₃H₇ O Q20 2-CH₃-4-CF₂CF₃ 1525i-C₃H₇ O Q20 2-CH₃-4-CF(CF₃)₂ 1526 i-C₃H₇ S Q20 2-CH₃-4-CF₂CF₃ 1527i-C₃H₇ S Q20 2-CH₃-4-CF(CF₃)₂ 1528 i-C₃H₇ NCH₃ Q20 2-CH₃-4-CF₂CF₃ 1529i-C₃H₇ NCH₃ Q20 2-CH₃-4-CF(CF₃)₂ 1530 i-C₃H₇ NPh Q20 2-CH₃-4-CF₂CF₃ 1531i-C₃H₇ NPh Q20 2-CH₃-4-CF(CF₃)₂ 1532 i-C₃H₇ O Q21 2-CH₃-4-CF₂CF₃ 1533i-C₃H₇ O Q21 2-CH₃-4-CF(CF₃)₂ 1534 i-C₃H₇ S Q21 2-CH₃-4-CF₂CF₃ 1535i-C₃H₇ S Q21 2-CH₃-4-CF(CF₃)₂ 1536 i-C₃H₇ NCH₃ Q21 2-CH₃-4-CF₂CF₃ 1537i-C₃H₇ NCH₃ Q21 2-CH₃-4-CF(CF₃)₂ 1538 i-C₃H₇ NPh Q21 2-CH₃-4-CF₂CF₃ 1539i-C₃H₇ NPh Q21 2-CH₃-4-CF(CF₃)₂ 1540 i-C₃H₇ O Q22 2-CH₃-4-CF₂CF₃ 1541i-C₃H₇ O Q22 2-CH₃-4-CF(CF₃)₂ 1542 i-C₃H₇ S Q22 2-CH₃-4-CF₂CF₃ 1543i-C₃H₇ S Q22 2-CH₃-4-CF(CF₃)₂ 1544 i-C₃H₇ NCH₃ Q22 2-CH₃-4-CF₂CF₃ 1545i-C₃H₇ NCH₃ Q22 2-CH₃-4-CF(CF₃)₂ 1546 i-C₃H₇ NPh Q22 2-CH₃-4-CF₂CF₃ 1547i-C₃H₇ NPh Q22 2-CH₃-4-CF(CF₃)₂

 

TABLE 32 (Z¹ = Z² = O, R² = R³ = H, Het = Q2, p = 0, B¹ = B⁴ = C)Physical property No R¹ Xn B² B³ Ym m.p. ° C. 1548 i-C₃H₇ H N C2-CH₃-4-OCH(CF₃)₂ 259-260 1549 C(CH₃)₂CH₂SCH₃ H N C 2-CH₃-4-OCH(CF₃)₂202-203 1550 C(CH₃)₂CH₂SCH₃ 5-Cl N C 2-CH₃-4-CF(CF₃)₂ 1551 i-C₃H₇ H N N2-CH₃-4-CF(CF₃)₂ 1552 i-C₃H₇ 5-Cl C N 2-CH₃-4-CF₂CF₃ 1553 i-C₃H₇ 5-I C N4-OCH(CF₃)₂ 1554 CH(CH₃)CH₂SCH₃ H N N 4-OCHF₂ 1555 C(CH₃)₂CH₂SOCH₃ H N C2-CH₃-4-OCF₃ 1556 CH(CH₃)CH(CH₃)SCH₃ H N C 2-CH₃-4-CF₂CF₃

 

TABLE 33 (Z¹ = Z² = O, R² = R³ = H, Het = Q3, p = 0, B¹ = B⁴ = C)Physical property No R¹ Xn B² B³ Ym m.p. ° C. 1557 i-C₃H₇ H N C2-CH₃-4-OCH(CF₃)₂ 1558 C(CH₃)₂CH₂SCH₃ H N C 2-CH₃-4-OCH(CF₃)₂ 1559C(CH₃)₂CH₂SCH₃ 2-Cl N C 2-CH₃-4-CF(CF₃)₂ 1560 i-C₃H₇ H N N2-CH₃-4-CF(CF₃)₂ 1561 i-C₃H₇ 2-Cl C N 2-CH₃-4-CF₂CF₃ 1562 i-C₃H₇ 2-I C N4-OCH(CF₃)₂ 1563 CH(CH₃)CH₂SCH₃ H N N 4-OCHF₂ 1564 C(CH₃)₂CH₂SOCH₃ H N C2-CH₃-4-OCF₃ 1565 CH(CH₃)CH(CH₃)SCH₃ H N C 2-CH₃-4-CF₂CF₃

In the Tables 1 to 33, “Ac” means acetyl group, “Ph” means phenyl groupand “c-” means alicyclic hydrocarbon group.

The agricultural and horticultural insecticides containing theheterocyclic dicarboxylic acid diamide derivative of formula (I) of thepresent invention as an active ingredient are suitable for controllingvarious insect pests such as agrohorticultural insect pests, storedgrain insect pests, sanitary insect pests, nematodes, etc., which areinjurious to paddy rice, fruit trees, vegetables, other crops, flowers,ornamental plants, etc. They have a marked insecticidal effect, forexample, on LEPIDOPTERA including summer fruit tortrix (Adoxophes oranafasciata), smaller tea tortrix (Adoxophyes sp.), Manchurian fruit moth(Grapholita inopinata), oriental fruit moth (Grapholita molesta) soybeanpod border (Leguminovora glycinivorella), mulberry leafroller(Olethreutes mori), tea leafroller (Caloptilia thevivora), Caloptiliasp. (Caloptilia zachrysa), apple leafminer (Phyllonorvcter ringoniella),pear barkminer (Spulerrina astaurota), common white (Piers rapaecrucivora), tobacco budworm (Heliothis sp.), codling moth (Laspey resiapomonella), diamondback moth (Plutella xylostella), apple fruit moth(Argyresthia conjugella), peach fruit moth (Carposina niponensis), ricestem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocismedinalis), tobacco moth (Ephestia elutella), mulberry pyralid(Glyphodes pyloalis), yellow rice borer (Scirpophaga incertulas) riceskipper (Parnara guttata), rice armyworm (Pseudaletia separata), pinkborer (Sesamia inferens), common cutworm (Spodoptera litura), beetarmyworm (Spodoptera exigua), etc.; HEMIPTERA including aster leafhopper(Macrosteles fascifrons), green rice leafhopper (Nephotettixcincticepts), brown rice planthopper (Nilaparvata lugens), whitebackedrice planthopper (Sogatella furcifera), citrus psylla (Diaphorinacitri), grape whitefly (Aleurolibus taonabae), sweetpotato whitefly(Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum),turnup aphid (Lipaphis erysimi), green peach aphid (Myzus persicae),Indian wax scale (Ceroplastes ceriferus), cottony citrus scale(Pulvinaria aurantii) camphor scale (Pseudaonidia duplex), san Josescale (Comstockaspis perniciosa), arrowhead scale (Unapsis yanonensis)etc.; TYLENCHIDA including soybean beetle (Anomala rufocuprea), Japanesebeetle (Popillia japonica), tobacco beetle (Lasioderma serricorne),powderpost beetle (Lyctus brunneus), twenty-eight-spotted ladybird(Epilachna vigintiotopunctata), azuki bean weevil (Callosobruchuschinensis), vegetable weevil (Listroderes costirostris), maize weevil(Sitophilus zeamais), boll weevil (Anthonomus gradis gradis), rice waterweevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophorafemoralis), rice leaf beetle (Oulema oryzae), striped flea beetle(Phyllotreta striolata) pine shoot beetle (Tomicus piniperda), Coloradopotato beetle (Leptinotarsa decemlineata), Mexican bean beetle(Epilachna varivestis), corn rootworm (Diabrotica sp.), etc.; DIPTERAincluding (Dacus(Zeugodacus) cucurbitae), oriental fruit fly(Dacus(Bactrocera) dorsalis) rice leafminer (Agnomyza oryzae), onionmaggot (Delia antiqua), seedcorn maggot (Delia platura), soybean podgall midge (Asphondylia sp.), muscid fly (Musca domestica), housemosquito (Culex pipiens pipiens), etc.; and TYLENCHIDA including coffeeroot-lesion nematode (Pratylenchus coffeae), potato cyst nematode(Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrusnematode (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchusavenae), chrysanthemum foliar (Aphelenchoides ritzemabosi), etc.

The agricultural and horticultural insecticide containing theheterocyclic dicarboxylic acid diamide derivative represented by formula(I) of the present invention has a marked controlling effect on theabove-exemplified insect pests, sanitary pests and/or nematodes, whichare injurious to paddy field crops, upland crops, fruit trees,vegetables and other crops, flowers and ornament plants, and the like.Therefore, the desired effect of the agrohorticultural insecticide ofthe present invention can be exhibited by applying the insecticide tothe paddy field water, stalks and leaves or soil of paddy field, uplandfield, fruit trees, vegetables, other crops or flowers and ornamentplants at a season at which the insect pests, sanitary pests ornematodes are expected to appear, before their appearance or at the timewhen their appearance is confirmed.

In general, the agricultural and horticultural insecticide of thepresent invention is used after being prepared into conveniently usableforms according to ordinary manner for preparation of agrochemicals.

That is, the heterocyclic dicarboxylic acid diamide derivative offormula (I) and an appropriate carrier are blended optionally togetherwith an adjuvant in a proper proportion and prepared into a suitablepreparation form such as suspension, emulsifiable concentrate, solubleconcentrate, wettable powder, granules, dust or tablets throughdissolution, separation, suspension, mixing, impregnation, adsorption orsticking.

The inert carrier used in the present invention may be either solid orliquid. As the solid carrier, soybean flour, cereal flour, wood flour,bark flour, saw dust, powdered tobacco stalks, powdered walnut shells,bran, powdered cellulose, extraction residues of vegetables, powderedsynthetic polymers or resins, clay (e.g. kaolin, bentonite and acidclay), talc (e.g. talc and pyrophyllite), silica materials (e.g.diatomaceous earth, siliceous sand, mica, white carbon, i.e. synthetichigh-dispersion silicic acid, also called finely divided hydrated silicaor hydrated silicic acid, some of the commercially available productscontain calcium silicate as the major component), activated carbon,powdered sulfur, pumice, calcined diatomaceous earth, ground brick, flyash, sand, calcium carbonate, calcium phosphate and other inorganic ormineral powders, chemical fertilizers such as ammonium sulfate, ammoniumphosphate, ammonium nitrate, urea, ammonium chloride and the like, andcompost. These carriers may be used either alone or as a mixture of twoor more carriers.

The liquid carrier is that which itself has a solubility or which iswithout such solubility but is capable of dispersing an activeingredient with the aid of an adjuvant. The following are typicalexamples of the liquid carrier and can be used alone or as a mixturethereof. Water; alcohols such as methanol, ethanol, isopropanol, butanoland ethylene glycol; ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers suchas ethyl ether, dioxane, cellosolve, dipropyl ether and tetrahydrofuran;aliphatic hydrocarbons such as kerosene and mineral oil; aromatichydrocarbons such as benzene, toluene, xylene, solvent naphtha andalkylnaphthalene; halogenated hydrocarbons such as dichlorethane,chloroform, carbon tetrachloride and chlorobenzene; esters such as ethylacetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate;amides such as dimethylformamide, diethylformamide anddimethylacetamide; nitriles such as acetonitrile; and dimethylsulfoxide.

The following are typical examples of the adjuvant, which are useddepending upon purposes and used alone or in combination of two or moreadjuvants in some cases, or need not to be used at all.

To emulsify, disperse, dissolve and/or wet an active ingredient, asurfactant is used. As the surfactant, there can be exemplifiedpolyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers,polyoxyethylene higher fatty,acid esters, polyoxyethylene resinates,polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitanmonooleate, alkylarylsulfonates, naphthalene-sulfonic acid condensationproducts, ligninsulfonates and higher alcohol sulfate esters.

Further, to stabilize the dispersion of an active ingredient, tackify itand/or bind it, there may be used adjuvants such as casein, gelatin,starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinylalcohols, turpentine, bran oil, bentonite and ligninsulfonates.

To improve the flowability of a solid product, there may be usedadjuvants such as waxes, stearates and alkyl phosphates.

Adjuvants such as naphthalenesulfonic acid condensation products andpolycondensates of phosphates may be used as a peptizer for dispersibleproducts.

Adjuvants such as silicone oil may also be used as a defoaming agent.

The content of the active ingredient may be varied according to theneed. In dusts or granules, the suitable content thereof is from 0.01 to50% by weight. In emulsifiable concentrate and flowable wettable powder,too, the suitable content is from 0.01 to 50% by weight.

The agricultural and horticultural insecticide of the present inventionis used to control a variety of insect pests in the following manner.That is, it is applied to a crop on which the insect pests are expectedto appear or a site where appearance of the insect pests is undesirable,as it is or after being properly diluted with or suspended in water orthe like, in an amount effective for control of the insect pests.

The applying dosage of the agrihorticultural insecticide of the presentinvention is varied depending upon various factors such as a purpose,insect pests to be controlled, a growth state of a plant, tendency ofinsect pests appearance, weather, environmental conditions, apreparation form, an application method, an application site and anapplication time. It may be properly chosen in a range of 0.1 g to 10 kg(in terms of active ingredient compound) per 10 are depending uponpurposes.

The agricultural and horticultural insecticide of the present inventionmay be used in admixture with other agricultural and horticulturaldisease or pest controllers in order to expand both spectrum ofcontrollable diseases and insect pest species and the period of timewhen effective applications are possible or to reduce the dosage.

EXAMPLES

Typical examples of the present invention are described below, but theyshould not be construed as limiting the scope of the invention.

Example 1 (1-1). Production ofN-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-3,4-dicarboximide

In 10 ml of THF were dissolved 1.50 g of pyridine-3,4-dicarboxylic acidanhydride and 2.75 g of 4-(heptafluoro-2-propyl)-2-methylaniline, andthe reaction was carried out at room temperature for 3 hours. Aftercompletion of the reaction, the solvent was distilled off under reducedpressure and 20 ml of trifluoroacetic anhydride was added to theresulting residue, and the reaction was carried out with refluxing for 3hours. After completion of the reaction, the solvent was distilled offunder reduced pressure to obtain crudeN-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-3,4-dicarboximidequantitatively.

(1-2). Production of3-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-4-pyridinecarboxylicacid-2-propylamide (Compound No. 230) and4-[4-(heptafluoro-2-propyl)-2-methylphenyl]amino-carbonyl-3-pyridinecarboxylicacid-2-propylamide (Compound No. 512)

In 10 ml of dioxane was dissolved 4.1 g ofN-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-3,4-dicarboximide,followed by adding thereto 0.8 g of isopropylamine, and the reaction wascarried out at room temperature for 8 hours. After completion of thereaction, the solvent was distilled off under reduced pressure and theresulting residue was purified by a silica gel column chromatographyusing a 2:1 mixed solvent of hexane and ethyl acetate as an eluent, toobtain 2.1 g of (compound No. 230) and 1.8 g of (compound No. 512) aswhite crystals.

Physical property: compound No. 230 m.p. 234-236° C. Yield 45%. compoundNo. 512 m.p. 206-208° C. Yield 39%.

Example 2 (2-1). Production of5-bromo-3-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-1-phenyl-4-pyrazolecarboxylicacid 2-propylamide (Compound No. 1382) and5-bromo-4-[4-(heptafluoro-2-propyl)-2-methylphenyl]-aminocarbonyl-1-phenyl-3-pyrazolecarboxylicacid 2-propylamide (Compound No. 1414)

In 10 ml of thionyl chloride was dissolved 500 mg of5-bromo-1-phenyl-3,4-pyrazoledicarboxylic acid, and the reaction wascarried out at reflux temperature for 2 hours. After completion of thereaction, the thionyl chloride was distilled off under reduced pressureto obtain a crude acid chloride. This compound was dissolved in 2 ml ofTHF and the resulting solution was added dropwise at 0° C. to a solutionprepared by dissolving 420 mg of heptafluoro-2-propyl-2-methylanilineand 410 mg of triethylamine in 10 ml of THF. After completion of thedropwise addition, 470 mg of isopropylamine was added thereto at 0° C.and the reaction was carried out at room temperature for 2 hours. Aftercompletion of the reaction, the triethylamine hydrochloride was filteredoff and the mother liquor was concentrated. The resulting residue waspurified by a silica gel column chromatography using ethylacetatein-hexane as an eluent, to obtain 360 mg of5-bromo-3-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-1-phenyl-4-pyrazole-carboxylicacid 2-propylamide (compound No. 1382) and 360 mg of5-bromo-4-[4-(heptafluoro-2-propyl)-2-methylphenyl]-aminocarbonyl-1-phenyl-3-pyrazole-carboxylicacid 2-propylamide (compound No. 1414) as white crystals.

Physical property:

compound No. 1382 m.p. 164-166. Yield 36%.

compound No. 1414 m.p. 167-169. Yield 36%.

Example 3 (3-1). Production of2-chloro-4-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-3-pyridinecarboxylicacid

In 20 ml of anhydrous THF was dissolved 2.78 g of diisopropylamine, and18 ml of a solution of n-butyllithium in hexane (1.53 M) was addeddropwise thereto at −78° C. under an argon atmosphere. The resultingmixture was stirred at −78° C. for 1 hour, and then a solution of 5.17 gof 2-chloro-4-pyridinecarboxylic acid4-(heptafluoro-2-propyl)-2-methylanilide in 100 ml of THF was addeddropwise thereto at −78° C. After completion of the dropwise addition,the stirring was continued at −78° C. for 2 hours and carbon dioxide gaswas bubbled thereinto for 1 hour. Then, the resulting mixture was warmedto room temperature and 200 ml of 1N hydrochloric acid was addedthereto, followed by extraction with ethyl acetate. The organic layerwas dried over anhydrous magnesium sulfate and then distilled underreduced pressure to remove the solvent, whereby 4.70 g (yield: 82%) ofthe crude desired compound was obtained as an amorphous solid. Thiscompound was used in a subsequent reaction without purification.

(3-2). Production of2-chloro-4-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-3-pyridinecarboxylicacid 2-propylamide (Compound No. 524)

In 10 ml of t-butyl methyl ether was dissolved 500 mg of2-chloro-4-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-3-pyridinecarboxylicacid, followed by adding thereto 340 mg of ok trifluoroacetic anhydride,and the resulting mixture was stirred at room temperature for 2 hours.After the disappearance of the starting material was confirmed by TLC,330 mg of isopropylamine was added to the mixture, followed by stirringat room temperature for another 2 hours. After completion of thereaction, ethyl acetate was added and the reaction solution was washedsuccessively with water, a saturated aqueous sodium hydrogencarbonatesolution and a saturated aqueous sodium chloride solution, and driedover anhydrous magnesium sulfate. The solvent was distilled off underreduced pressure and the resulting residue was purified by a silica gelcolumn chromatography using ethyl acetate/n-hexane as an eluent, toobtain 460 mg of the desired compound as white crystals.

Physical property: m.p. 275-277° C. Yield 84%.

Example 4 (4-1). Production ofN-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-2,3-dicarboximide-1-oxide

In 25 ml of chloroform was dissolved 3.1 g ofN-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-2,3-dicarboximide,and 5.0 g of m-chloroperbenzoic acid was added thereto at roomtemperature. After the resulting mixture was stirred at room temperaturefor 3 hours, a saturated aqueous sodium hydrogencarbonate solution wasadded to the reaction solution, followed by extraction with ethylacetate. The organic layer was washed successively with water, asaturated aqueous sodium hydrogencarbonate solution and a saturatedaqueous sodium chloride solution, and dried over anhydrous magnesiumsulfate. The solvent was distilled off under reduced pressure and theresulting residue was purified by a silica gel column chromatographyusing ethyl acetate/n-hexane as an eluent, to obtain 820 mg (yield: 84%)of the desired compound.

(4-2). Production of3-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-2-(2-propyl)amino-carbonylpyridine-N-oxide(Compound No. 804)

In 10 ml of THF was dissolved 400 mg ofN-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-2,3-dicarboximide-1-oxide,followed by adding thereto 200 mg of isopropylamine, and the resultingmixture was stirred at room temperature for 5 hours. After completion ofthe reaction, the solvent was distilled off under reduced pressure andthe resulting residue was purified by a silica gel column chromatographyusing ethyl acetate/n-hexane as an eluent, to obtain 290 mg of thedesired compound as white crystals.

Physical property: m.p. 108-110° C. Yield 63%.

Typical formulation examples and test examples of the present inventionare described below but they should not be construed as limiting thescope of the invention.

In the formulation examples, parts are all by weight.

Formulation Example 1

Each compound listed in Tables 1 to 33 50 parts Xylene 40 parts Mixtureof polyoxyethylene nonylphenyl ether and calcium 10 partsalkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the aboveingredients to effect dissolution.

Formulation Example 2

Each compound listed in Tables 1 to 33 3 parts Clay powder 82 partsDiatomaceous earth powder 15 parts

A dust was prepared by mixing uniformly and grinding the aboveingredients.

Formulation Example 3

Each compound listed in Tables 1 to 33 5 parts Mixed powder of bentoniteand clay 90 parts Calcium lignin sulfonate 5 parts

Granules were prepared by mixing the above ingredients uniformly, andkneading the resulting mixture together with a suitable amount of water,followed by granulation and drying.

Formulation Example 4

Each compound listed in Tables 1 to 33 20 parts Kaolin and synthetichigh-dispersion silicic acid 75 parts Mixture of polyoxyethylenenonylphenyl ether and calcium 5 parts alkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding theabove ingredients.

Test Example 1

Insecticidal Effect on Diamondback Moth (Plutella xylostella)

Adult diamondback moths were released and allowed to oviposit on aChinese cabbage seedling. Two days after the release, the seedlinghaving eggs deposited thereon was immersed for about 30 seconds in aliquid chemical prepared by diluting a preparation containing each ofthe compounds listed in Tables 1 to 33 as an active ingredient to adjustthe concentration to 500 ppm. After air-drying, the seedling was allowedto stand in a room thermostated at 25° C. Six days after the immersionin the liquid chemical, the hatched insects were counted and themortality was calculated according to the following equation. The testwas carried out with three replications of 10 insects. $\begin{matrix}{\quad {Corrected}} \\{{mortality}{\quad \quad}(\%)}\end{matrix} = {\frac{\begin{bmatrix}{\quad {{Number}\quad {of}}} \\{{hatched}\quad {insects}} \\{\quad {{in}\quad {untreated}}} \\{\quad {group}}\end{bmatrix} - \begin{bmatrix}{\quad {{Number}\quad {of}}} \\{{hatched}\quad {insects}} \\{\quad {{in}\quad {treated}}} \\{\quad {group}}\end{bmatrix}}{\begin{bmatrix}{\quad {{Number}\quad {of}}} \\{{hatched}\quad {insects}} \\{\quad {{in}\quad {untreated}}} \\{\quad {group}}\end{bmatrix}} \times 100}$

Physical property:

compound No. 1382 m.p. 164-166. Yield 36%.

compound No. 1414 m.p. 167-169. Yield 36%.

Test Example 2 Insecticidal Effect on Smaller Tea Tortrix (Adoxophyessp.)

A tea leaf was immersed for about 30 seconds in a liquid chemicalprepared by diluting a preparation containing each of the compoundslisted in Tables 1 to 33 as an active ingredient to adjust theconcentration to 500 ppm. After air-drying, the leaf was placed in aplastic Petri dish with a diameter of 9 cm and inoculated with larvae ofsmaller tea tortrix, and the Petri dish was allowed to stand in a roomthermostated at 25° C. and having a humidity of 70%. Eight days afterthe inoculation, the dead and alive were counted and the mortality wascalculated according to the following equation. The test was carried outwith three replications of 10 insects. $\begin{matrix}{Corrected} \\{{mortality}\quad (\%)}\end{matrix} = {\frac{\begin{bmatrix}{{Number}\quad {of}\quad {sur}\text{-}} \\{{viving}\quad {insects}} \\{{in}\quad {untreated}} \\{group}\end{bmatrix} - \begin{bmatrix}{{Number}\quad {of}\quad {sur}\text{-}} \\{{viving}\quad {insects}} \\{{in}\quad {treated}} \\{group}\end{bmatrix}}{\begin{bmatrix}{{Number}\quad {of}\quad {sur}\text{-}} \\{{viving}\quad {insects}} \\{{in}\quad {untreated}} \\{group}\end{bmatrix}} \times 100}$

As a result, the following compounds were found to have a correctedmortality of 90% or more: compound Nos. 13, 18, 55, 57, 127, 136, 230,464, 484, 512, 524, 737, 794, 795, 805, 821, 989, 1009, 1048, 1095,1127, 1189, 1204, 1220, 1247, 1249, 1251, 1255, 1303, 1313, 1473, 1505,1548 and 1549.

As described above, the agricultural and horticultural insecticidescontaining the heterocyclic dicarboxylic acid diamide derivative of thegeneral formula (I) of the present invention as an active ingredienthave an excellent controlling effect on insect pests such as diamondbackmoth, common cutworm, etc.

What is claimed is:
 1. A heterocyclic dicarboxylic acid diamidederivative represented by the formula (I):

{wherein R¹, R² and R³, which may be the same or different, are hydrogenatoms, (C₃-C₆)cycloalkyl groups, halo(C₃-C₆)cycloalkyl groups or—A¹—(R⁴)r (wherein A¹ is a (C₁-C₈)alkylene group, a (C₃-C₆)alkenylenegroup or a (C₃-C₆)alkynylene group, R⁴, which may be the same ordifferent, are hydrogen atoms; halogen atoms; cyano groups; nitrogroups; halo(C₁-C₆)alkyl groups; (C₃-C₆)cycloalkyl groups;halo(C₃-C₆)cycloalkyl groups; (C₁-C₆)alkoxycarbonyl groups;di(C₁-C₆)alkoxyphosphoryl groups whose (C₁-C₆)alkoxy groups may be thesame or different; di(C₁-C₆)alkoxythiophosphoryl groups whose(C₁-C₆)alkoxy groups may be the same or different; diphenylphosphinogroups; diphenylphosphono groups; phenyl groups; substituted phenylgroups having one or more substituents which may be the same ordifferent and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups;heterocyclic groups; substituted heterocyclic groups having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A²—R⁵ (wherein A² is —O—, —S—,—SO—, —SO₂—, —N(R⁶)— (wherein R is a hydrogen atom; a(C₁-C₆)alkylcarbonyl group; a halo(C₁-C₆)alkylcarbonyl group; a(C₁-C₆)alkoxycarbonyl group; a phenylcarbonyl group; a substitutedphenylcarbonyl group having one or more substituents which may be thesame or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aphenyl(C₁-C₄)alkoxycarbonyl group; a substitutedphenyl(C₁-C₄)alkoxycarbonyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a (C₁-C₆)alkylsulfonyl group; or ahalo(C₁-C₆)alkylsulfonyl group), —C(═O)— or —C(═NOR⁷)— (wherein R⁷ is ahydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a(C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynylgroup; a cyclo(C₃-C₆)alkyl group; a phenyl(C₁-C₄)alkyl group; or asubstituted phenyl(C₁-C₄)alkyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups), and R⁵ is a hydrogen atom; a(C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; ahalo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynylgroup; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a(C₁-C₆)alkoxy(C₁-C₆)alkyl group; a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; aformyl group; a (C₁-C₆)alkylcarbonyl group; a halo(C₁-C₆)alkylcarbonylgroup; a (C₁-C₆)alkoxycarbonyl group; a mono(C₁-C₆)alkylaminocarbonylgroup; a di(C₁-C₆)alkylaminocarbonyl group whose (C₁-C₆)alkyl groups maybe the same or different; a mono(C₁-C₆)alkylaminothiocarbonyl group; adi(C₁-C₆)alkylaminothiocarbonyl group whose (C₁-C₆)alkyl groups may bethe same or different; a di(C₁-C₆)alkoxyphosphoryl group whose(C₁-C₆)alkoxy groups may be the same or different; adi(C₁-C₆)alkoxythiophosphoryl group whose (C₁-C₆)alkoxy groups may bethe same or different; a phenyl group; a substituted phenyl group havingone or more substituents which may be the same or different and areselected from halogen atoms, (C₁-C₅)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a phenyl(C₁-C₄)alkyl group; asubstituted phenyl(C₁-C₄)alkyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a heterocyclic group; or a substitutedheterocyclic group having one or more substituents which may be the sameor different and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups), and ris an integer of 1 to 4), provided that R¹ and R² are not hydrogen atomsat the same time, R¹ and R² together with the N to which they areattached may form a 4 to 7 membered ring by combining to each other, inwhich the ring may contain the same or different 1 to 3 hetero atomsselected from the group consisting of oxygen atom, sulfur atom andnitrogen atom, Het is a heterocyclic group represented by any of thefollowing formulas Q1 to Q4:

 (wherein X, which may be the same or different, are halogen atoms;cyano groups; nitro groups; (C₃-C₆)cycloalkyl groups;halo(C₃-C₆)cycloalkyl groups; tri(C₁-C₆)alkylsilyl groups whose(C₁-C₆)alkyl groups may be the same or different; phenyl groups;substituted phenyl groups having one or more substituents which may bethe same or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups;heterocyclic groups; substituted heterocyclic groups having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A³—R⁸ wherein A³ is —O—, —S—,—SO—, —SO₂—, —N(R⁶)— (wherein R⁶ is as defined above), —C(═O)—,—C(═NOR⁷)— (wherein R⁷ is as defined above), a (C₁-C₆)alkylene group, ahalo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylene group, ahalo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R⁸ is as follows: (1) when A³ is —O—,—S—, —SO—, —SO₂— or —N(R⁶)— (wherein R⁶ is as defined above), then R⁸ isa halo(C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkenyl group; a phenylgroup; a substituted phenyl group having one or more substituents whichmay be the same or different and are selected from halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthiogroups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; a substituted heterocyclic group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A⁴—R⁹ (wherein A⁴ is a(C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₃-C₆)alkenylenegroup, a halo(C₃-C₆)alkenylene group, a (C₃-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R⁹ is a hydrogen atom; a halogen atom;a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a(C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted phenyl grouphaving one or more substituents which may be the same or different andare selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A⁵—R¹⁰ (wherein A⁵ is —O—, —S—,—SO—, —SO₂— or —C(═O), and R¹⁰ is a (C₁-C₆)alkyl group; ahalo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenylgroup; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; aphenyl group; a substituted phenyl group having one or more substituentswhich may be the same or different and are selected from halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthiogroups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; or a substituted heterocyclic group having one ormore substituents which may be the same or different and are selectedfrom halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups)), (2) when A³ is —C(═O)— or —C(═NOR⁷)—(wherein R⁷ is as defined above), then R⁸ is a hydrogen atom; a(C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₂C₆)alkenyl group; ahalo(C₂C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; ahalo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a (C₁-C₆)alkylthiogroup; a mono(C₁-C₆)alkylamino group; a di(C₁-C₆)alkylamino group whose(C₁-C₆)alkyl groups may be the same or different; a phenyl group; asubstituted phenyl group having one or more substituents which may bethe same or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aphenylamino group; a substituted phenylamino group having on the ringone or more substituents which may be the same or different and areselected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a heterocyclic group; or a substitutedheterocyclic group having one or more substituents which may be the sameor different and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups, and (3)when A³ is a (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a(C₂-C₆)alkenylene group, a halo(C₂-C₆)alkenylene group, a(C₂-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group, then R⁸ is ahydrogen atom; a halogen atom; a (C₃-C₆)cycloalkyl group; ahalo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; atri(C₁-C₆)alkylsilyl group whose (C₁-C₆)alkyl groups may be the same ordifferent; a phenyl group; a substituted phenyl group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a heterocyclic group; a substitutedheterocyclic group having one or more substituents which may be the sameor different and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; or—A—R¹¹ (wherein A⁶ is —O—, —S—, —SO— or —SO₂—, and R¹¹ is a(C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a phenyl group;a substituted phenyl group having one or more substituents which may bethe same or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; a substituted heterocyclic group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A⁷—R¹² (wherein A⁷ is a(C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylenegroup, a halo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R¹² is a hydrogen atom; a halogen atom;a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a(C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthiogroup; a halo(C₁-C₆)alkylthio group; a (C₁-C₆)alkylsulfinyl group; ahalo(C₁-C₆)alkylsulfinyl group; a (C₁-C₆)alkylsulfonyl group; ahalo(C₁-C₆)alkylsulfonyl group; a phenyl group; a substituted phenylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aphenoxy group; a substituted phenoxy group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₈)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₅)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a phenylthio group; a substitutedphenylthio group having one or more substituents which may be the sameor different and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; aheterocyclic group; or a substituted heterocyclic group having one ormore substituents which may be the same or different and are selectedfrom halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups)), and n is an integer of 0 to 3, X mayform a condensed ring selected from the group consisting of indole ring,benzo[b]furan ring, benzo[b]thiophene ring, quinoline ring, isoquinolinering, naphthyridine ring, quinoxaline ring and cinnoline ring, bycombining together with the adjacent atoms in the heterocyclic ring, andsaid condensed ring may have one or more substituents, which may be thesame or different, and are selected from halogen atoms; (C₁-C₆)alkylgroups; halo(C₁-C₆)alkyl groups; (C₁-C₆)alkoxy groups; halo(C₁-C₆)alkoxygroups; (C₁-C₆)alkylthio groups; halo(C₁-C₆)alkylthio groups;(C₁-C₆)alkylsulfinyl groups; halo(C₁-C₆)alkylsulfinyl groups;(C₁-C₆)alkylsulfonyl groups; halo(C₁-C₆)alkylsulfonyl groups; phenylgroup; substituted phenyl groups having one or more substituents whichmay be the same or different and are selected from halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthiogroups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups;heterocyclic groups; and substituted heterocyclic groups having one ormore substituents which may be the same or different and are selectedfrom halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups, W is O, S or N—R¹³ (wherein R¹³ is a(C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; ahalo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynylgroup; a (C₁-C₆)alkoxy group; a phenyl group; a substituted phenyl grouphaving one or more substituents which may be the same or different andare selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a phenyl(C₁-C₆)alkyl group; or asubstituted phenyl(C₁-C₆)alkyl group having on the ring one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups), and p and q, which may be the same ordifferent, are integers of 0 to 1), B¹, B², B³ and B⁴, which may be thesame or different, are carbon atoms, Y, which may be the same ordifferent, are halogen atoms; cyano groups; nitro groups;halo(C₃-C₆)cycloalkyl groups; phenyl groups; substituted phenyl groupshaving one or more substituents which may be the same or different andare selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; heterocyclic groups; substitutedheterocyclic groups having one or more substituents which may be thesame or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; or—A³—R³ (wherein A³ and R⁸ are as defined above), and m is an integer of1 to 5, Y may form a condensed ring by combining together with theadjacent carbon atoms in the aromatic ring, and said condensed ring mayhave one or more substituents, which may be the same or different, andare selected from halogen atoms; (C₁-C₆)alkyl groups; halo(C₁-C₆)alkylgroups; (C₁-C₆)alkoxy groups; halo(C₁-C₆)alkoxy groups; (C₁-C₆)alkylthiogroups; halo(C₁-C₆)alkylthio groups; (C₁-C₆)alkylsulfinyl groups;halo(C₁-C₆)alkylsulfinyl groups; (C₁-C₆)alkylsulfonyl groups;halo(C₁-C₆)alkylsulfonyl groups; phenyl group; substituted phenyl groupshaving one or more substituents which may be the same or different andare selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; heterocyclic groups; and substitutedheterocyclic groups having one or more substituents which may be thesame or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups, andeach of Z¹ and Z² is an oxygen atom or a sulfur atom, provided that: (1)when Het is Q2, and B¹, B², B³ and B⁴ are carbon atoms at the same time,then Ym is other than 3-chloro-2-methyl group, 3-chloro-2,6-diethylgroup, 5chloro-2-methyl group, 2,6-diethyl group, 4-chloro-2-fluorogroup and 2-ethyl-6-methyl group, and (2) when Het is Q4 and B¹, B², B³and B⁴ are carbon atoms at the same time, then Ym is other than2,5-dichloro group, 2,4-difluoro group, 2,6-difluoro group,3-chloro-2-methyl group, 5-chloro-2-methyl group, 5-fluoro-2-methylgroup, 2,6-dimethyl group, 2,6-diethyl group, 2-ethyl-6-methyl group,2-methoxy-5-nitro group, 2-methoxy-5methyl group, 2,6-diethoxy group,3-bromo-2-methyl group, 3-fluoro-2-methyl group, 3-iodo-2-methyl group,3-cyano-2-methyl group, 3-difluoromethoxy-2-methyl group,5-chloro-2-ethyl group, 2,5-dimethyl group, 2,3-dichloro group,3-chloro2,6-diethyl group, 4-trifluoromethyl group,3-methoxycarbonyl-2-methyl group, 3-trifluoromethyl-2-methyl group,3,5-dichloro-2,6diethyl group, 3,4-dichloro group,3-(methoxycarbonylmethyloxy)-2-methyl group, 2-methyl-3-nitro group and4-trifluoromethoxy group.
 2. A heterocyclic dicarboxylic acid diamidederivative according to claim 1, wherein Het is Q1, Q2, Q3 or Q4, R¹ isa (C₃-C₆)cycloalkyl group, a halo(C₃-C₆)cycloalkyl group or —A¹—(R⁴)r(wherein A¹ is a (C₁-C₈)alkylene group, R⁴, which may be the same ordifferent, are hydrogen atoms; halogen atoms; cyano groups; nitrogroups; (C₁-C₆)alkoxycarbonyl groups; di(C₁-C₆)alkoxyphosphoryl groupswhose (C₁-C₆)alkoxy groups may be the same or different;di(C₁-C₆)alkoxythiophosphoryl groups whose (C₁-C₆)alkoxy groups may bethe same or different; phenyl groups; substituted phenyl groups havingone or more substituents which may be the same or different and areselected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkylgroups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; pyridyl groups; substituted pyridylgroups having one or more substituents which may be the same ordifferent and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; or—A²—R⁵ (wherein A² is —O—, —S—, —SO—, —SO₂—, —N(R⁶)— (wherein R⁶ is ahydrogen atom, a (C₁-C₆)alkylcarbonyl group, a halo(C₁-C₆)alkylcarbonylgroup or a (C₁-C₆)alkoxycarbonyl group), or —C(═NOR⁷)— (wherein R⁷ is ahydrogen atom, a (C₁-C₆)alkyl group or a halo(C₁-C₆)alkyl group), and R⁵is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a(C₁-C₆)cycloalkyl group; a halo(C₁-C₆)cycloalkyl group; a phenyl group;a substituted phenyl group having one or more substituents which may bethe same or different and are selected from halogen atoms, (C₁-C₆)alkylgroups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxygroups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; apyridyl group; or a substituted pyridyl group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups), and r is an integer of 1 to 4), R² andR³, which may be the same or different, are hydrogen atoms or(C₁-C₆)alkyl groups, X and Y, which may be the same or different, arehalogen atoms; cyano groups; nitro groups; phenyl groups; substitutedphenyl groups having one or more substituents which may be the same ordifferent and are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; pyridylgroups; substituted pyridyl groups having one or more substituents whichmay be the same or different and are selected from halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthiogroups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; or—A³—R⁸ [wherein A³ is —O—, —S—, —SO—, —SO₂—, a (C₁-C₆)alkylene group, ahalo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylene group, ahalo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R⁸ is as follows: (1) when A³ is —O—,—S—, —SO— or —SO₂—, then R⁸ is a phenyl group; a substituted phenylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; apyridyl group; a substituted pyridyl group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; or —A⁴—R⁹ (wherein A⁴ is a(C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₃-C₆)alkenylenegroup, a halo(C₃-C₆)alkenylene group, a (C₃-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, and R⁹ is a hydrogen atom, a halogen atomor —A⁵—R¹⁰ (wherein A⁵ is —O—, —S—, —SO— or —SO₂—, and R¹⁰ is a(C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a (C₃-C₆)alkenyl group, ahalo(C₃-C₆)alkenyl group, a (C₃-C₆)cycloalkyl group or ahalo(C₃-C₆)cycloalkyl group)), and (2) when A³ is a (C₁-C₆)alkylenegroup, a halo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylene group, ahalo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or ahalo(C₃-C₆)alkynylene group, then R⁸ is a hydrogen atom; a halogen atom;a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; atri(C₁-C₆)alkylsilyl group whose (C₁-C₆)alkyl groups may be the same ordifferent; a phenyl group; a substituted phenyl group having one or moresubstituents which may be the same or different and are selected fromhalogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups andhalo(C₁-C₆)alkylsulfonyl groups; a pyridyl group; a substituted pyridylgroup having one or more substituents which may be the same or differentand are selected from halogen atoms, (C₁-C₆)alkyl groups,halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,(C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,(C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; or—A⁶—R¹¹ (wherein A⁶ is —O—, —S—, —SO— or —SO₂—, and R¹¹ is —A⁷—R¹²(wherein A⁷ is a (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a(C₂-C₆)alkenylene group, a halo(C₂-C₆)alkenylene group, a(C₂-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group, and R¹² is ahydrogen atom, a halogen atom, a (C₁-C₆)alkoxy group, ahalo(C₁-C₆)alkoxy group, a (C₁-C₆)alkylthio group, ahalo(C₁-C₆)alkylthio group, a (C₁-C₆)alkylsulfinyl group, ahalo(C₁-C₆)alkylsulfinyl group, a (C₁-C₆)alkylsulfonyl group or ahalo(C₁-C₆)alkylsulfonyl group))], both B¹ and B⁴ are carbon atoms, B²and B³, which may be the same or different, are carbon atoms or nitrogenatoms, and each of Z¹ and Z² is an oxygen atom.
 3. A heterocyclicdicarboxylic acid diamide derivative according to claim 2, wherein X,which may be the same or different, are halogen atoms, nitro groups,halo(C₁-C₆)alkyl groups, halo(C₁-C₆)alkoxy groups orhalo(C₁-C₆)alkylthio groups, and n is an integer of 0 to
 3. 4. Aheterocyclic dicarboxylic acid diamide derivative according to claim 3,wherein Y, which may be the same or different, are halogen atoms,(C₁-C₆)alkyl groups, halo(C₁-C₆)-alkyl groups, (C₁-C₆)alkoxy groups,halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthiogroups, halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkoxy groups,halo(C₁-C₆)-alkoxyhalo(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylsulfinylgroups or halo(C₁-C₆)alkylsulfonyl groups, and m is an integer of 1 to5.
 5. A heterocyclic dicarboxylic acid diamide derivative according toclaim 4, wherein R¹ is a (C₁-C₆)alkyl group, a (C₁-C₆)alkoxy(C₁-C₈)alkylgroup, a (C₁-C₆)alkylthio(C₁-C₈)-alkyl group, a(C₁-C₆)alkylsulfinyl(C₁-C₈)alkyl group or a(C₁-C₆)alkylsulfonyl(C₁-C₈)alkyl group, and R² and R³, which may be thesame or different, are hydrogen atoms or methyl groups.
 6. Anagricultural and horticultural insecticide characterized by containing aheterocyclic dicarboxylic acid diamide derivative according to claim 1as an active ingredient.
 7. A method for applying an agricultural andhorticultural insecticide, characterized by treating a crop to beprotected or soil with an effective amount of an agricultural andhorticultural insecticide according to claim 6 in order to protectuseful crops against insect pests.